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Silica Gel

Silica gel is a highly porous, amorphous form of silicon dioxide used in a variety of applications, including desiccants, chromatography, and catalysts.
It is characterized by a high surface area and the ability to adsorb water and other molecules.
Silica gel is commonly used in research and industry to remove moisture, purify substances, and facilitate chemical reactions.
Its unique properties make it a versatile material for a wide range of scientific and industrial processes.
Researchers can optimize their silica gel studies using PubCompare.ai's AI-driven comparison tools, which help identify the most reliable protocols from literature, preprints, and patents to enhance reproducibility and accuracy.

Most cited protocols related to «Silica Gel»

1
DNA Extraction and Sequencing Protocol for Plant Barcodes
Cited 90 times
Leaf tissues were first dried in silica gel. Ten milligrams of each of the dried tissues was rubbed for one minute at a frequency of 30 times/second in a FastPrep bead mill (Retsch MM400, Germany). DNA extractions were performed using the Plant Genomic DNA Kit (Tiangen Biotech Co., China) according to the manufacturer's instructions. The sequences of the universal primers for the DNA barcode to be tested, including those for psbA-trnH, matK, rbcL, rpoC1, ycf5 and ITS, and general PCR reaction conditions were obtained from previous studies [9] (link), [17] (link), [18] (link), [21] (link). Based on the conserved regions of 18S and 5.8S, we designed four pairs of primers for ITS1. Similarly, according to a previous study [25] (link) and the conserved regions of 5.8S and 26S, we also designed four pairs of primers for ITS2. PCR amplification was performed in 25-µl reaction mixtures containing approximately 30 ng of genomic DNA template, 1 X PCR buffer without MgCl2, 2.0 mM MgCl2, 0.2 mM of each dNTP, 0.1 µM of each primer (synthesized by Sangon Co., China) and 1.0 U Taq DNA Polymerase (Biocolor BioScience & Technology Co., China), with a Peltier Thermal Cycler PTC0200 (BioRad Lab, Inc., USA). Purified PCR products were sequenced in both directions with the primers used for PCR amplification on a 3730XL sequencer (Applied Biosystems, USA). To estimate the quality of the generated sequence traces, the original forward and reverse sequences were assembled using CodonCode Aligner 3.0 (CodonCode Co., USA). Base calling was carried out using the Phred program (version no. 0.020425.c). The quality values were defined for three levels: low quality (0 to 19 QV), medium quality (20 to 30 QV) and high quality (higher than 30 QV). The sequences showing >2 bases with a quality value below 20 QV in a 20-base window were trimmed. The forward and reverse reads have a minimum length of 100 bp, a minimum average QV of 30, and the post-trim lengths should be >50% of the original read length. In addition, the assembled contig should have a minimum average QV score of 40 and >50% overlap in the alignment of the forward and reverse reads. All sequences of the second set of plant samples containing the “internal transcribed spacer 2”or “psbA-trnH” were retrieved according to Keller et al. [42] (link) and GenBank annotations. Subsequences marked as ITS2 or psbA-trnH intergenic spacer were recovered after deleting sequences with ambiguous nucleotides and those shorter than 100 bp.
Chen S., Yao H., Han J., Liu C., Song J., Shi L., Zhu Y., Ma X., Gao T., Pang X., Luo K., Li Y., Li X., Jia X., Lin Y, & Leon C. (2010). Validation of the ITS2 Region as a Novel DNA Barcode for Identifying Medicinal Plant Species. PLoS ONE, 5(1), e8613.
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Publication 2010
Adjustment Disorders BP 100 Buffers DNA, Plant Genome Magnesium Chloride MATK protein, human Nucleotides Oligonucleotide Primers Plant Leaves Plants Silica Gel Taq Polymerase Tissues
2
Rearing Anopheles funestus Mosquitoes
Cited 55 times
Blood fed An. funestus adult females resting indoor were collected in houses between 06 and 12 AM in Tororo District (0°45′ N, 34°5′E) in Eastern Uganda, an area of high malaria transmission [2] (link). The collection was carried out in April and November 2009. Blood-fed and gravid mosquitoes resting inside houses were collected using aspirators and torches and immediately transported to the laboratory of the National Livestock Resources Research Institute based in Tororo. A new method was used to induce the females to lay eggs. Briefly, the collected blood fed females were stored in net covered paper cups or in cages and provided with cotton wool moistened with sucrose. They were maintained for 4 to 5 days to allow them to fully reach the gravid stage and were checked daily for survival. The gravid mosquitoes were then gently individually introduced into 1.5 ml Eppendorf tubes containing a 1square cm filter paper inserted into the bottom of the tube. The filter paper was moistened and excess water removed. The cap of the Eppendorf tube was pierced with 3 holes to allow air into the tube. The tubes were checked daily for the presence of eggs. Females that laid eggs were carefully removed from the tubes and transferred into Eppendorf tubes with silica gel. Eggs were stored at room temperature or at 4°C for up to 2 days and then sent via courier to the Liverpool School of Tropical Medicine (LSTM) where they were allowed to hatch in small cup and later transferred to larvae bowls for rearing. Apart from 20 families that were reared individually, the egg batches were pooled and reared together. Larvae were comparatively reared in mineral (bottled) and distilled water and fed abundantly with TetraminTM baby fish food every day. Water of each larvae bowl was changed every two days to reduce the mortality. The F1 adults generated were randomly mixed in cages for subsequent experiments.
Morgan J.C., Irving H., Okedi L.M., Steven A, & Wondji C.S. (2010). Pyrethroid Resistance in an Anopheles funestus Population from Uganda. PLoS ONE, 5(7), e11872.
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Publication 2010
Adult BLOOD Culicidae Females Fishes Gossypium Infant Food Larva Livestock Malaria Minerals Silica Gel Sucrose Transmission, Communicable Disease Woman
3
Radiochemical Synthesis of 89Zr Tracers
Cited 37 times

Protocol full text hidden due to copyright restrictions

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Publication 2009
carboxymethyl-chitin-glucan Cells chelex Esocidae Gamma Rays Hydrochloric acid Ions Medical Devices Mesylate, Deferoxamine Metals Oxalic Acids Pentetic Acid Phosphates Polytetrafluoroethylene Radioactivity Radionuclide Imaging Resins, Plant Saline Solution Silica Gel Solvents Spectrum Analysis Thin Layer Chromatography Yttrium
4
Blood Spot Storage and Preparation Protocols
Cited 37 times
For spot size measurements, fresh heparinized blood was spotted onto sheets of Whatman no 1, Whatman 3 MM (Whatman, Maidstone, UK) or glass fibre (Printed Filtermat A, Perkin Elmer, Beaconsfield, UK) filter paper in volumes from 1 μl to 45 μl. For antibody stability and recovery studies, reconstituted blood was prepared by mixing individual African malaria-hyperimmune plasma samples or a hyperimmune plasma pool or a European (non-exposed) negative control pool (all containing heparin) 1:1 by volume with washed European blood group O erythrocytes and immediately spotting 10 μl of this mixture onto Whatman 3 MM or glass fibre filter paper. Spots were allowed to dry at ambient temperature and relative humidity (RH) overnight.
Laboratory-generated blood spots and blood spots from Uganda were stored in individual self-sealing plastic bags (25 cm × 25 cm approx), which were then combined into sets and stored within three further successive plastic bags, the innermost of which contained approximately 3 g of self-indicating silica desiccant gel type III (Sigma). The bags were inspected regularly to confirm that the desiccant remained blue (RH < 20%), and the desiccant replaced if necessary.
Fingerprick blood samples from lower Moshi were collected into EDTA-coated microtainers and as blood spots on Whatman 3 MM paper and transported daily to the laboratory at Kilimanjaro Christian Medical College. Filter papers were refrigerated (2–8°C) in individual plastic bags with silica gel. Plasma was separated from packed red blood cells after centrifugation and stored at -20°C. All samples were assayed within 8 weeks of collection.
Corran P.H., Cook J., Lynch C., Leendertse H., Manjurano A., Griffin J., Cox J., Abeku T., Bousema T., Ghani A.C., Drakeley C, & Riley E. (2008). Dried blood spots as a source of anti-malarial antibodies for epidemiological studies. Malaria Journal, 7, 195.
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Publication 2008
BLOOD Centrifugation Desiccants Edetic Acid Erythrocytes Europeans Exanthema Heparin Humidity Immunoglobulins Malaria Negroid Races Phocidae Plasma Silica Gel
5
Robust Workflow for Comprehensive RNA Profiling
Cited 31 times
Total RNA was prepared from human cell lines (especially from the ATCC bio-resource center, N = 50) and tissue samples (clinical samples, N = 285) from 13 different human adult tissue types, i.e. blood, brain, breast, colon, epithelium, kidney, lymphoma, lung, liver, muscle, prostate, rectum and thyroid. RNA purification was performed by cesium chloride ultracentrifugation according to Chomczynski and Sacchi (26 (link)), by phenol-based extraction methods (TRIzol reagent, Invitrogen, USA), or silica gel-based purification methods (RNeasy Mini Kit, Qiagen, Germany; Strataprep kit, Stratagene, USA or SV RNA isolation kit, Promega, USA) according to the manufacturer's instructions with some modifications. Material was maintained at −80°C with minimal handling. RNA extraction was carried out in an RNase-free environment (see Supplementary Table 1 online).
The commercially available RNA samples were the ‘Universal Human Reference’ (N = 75) distributed by Stratagene (USA), and human brain (N = 2) and muscle (N = 2) RNAs supplied by Clontech (USA).
Once extracted, RNA concentration and purity was first verified by UV measurement, using the Ultrospec3100 pro (Amersham Biosciences, USA) and 5 mm cuvettes. The absorbance (A) spectra were measured from 200 to 340 nm. A230, A260 and A280 were determined. A260:A280 and A260:A230 ratios were calculated. For microcapillary electrophoresis measurements, the Agilent 2100 bioanalyzer (Agilent Technologies, USA) was used in conjunction with the RNA 6000 Nano and the RNA 6000 Pico LabChip kits. In total, 39 assays were run in accordance with the manufacturer's instructions (see Supplementary Notes online). To evaluate the reliability of the classifier systems described in this study, replicate runs were done on a set of 56 RNA samples loaded on different chips, resulting in 2 (N = 41), 3 (N = 12), 7 (N = 2) and 50 (N = 1) data points per sample.
Imbeaud S., Graudens E., Boulanger V., Barlet X., Zaborski P., Eveno E., Mueller O., Schroeder A, & Auffray C. (2005). Towards standardization of RNA quality assessment using user-independent classifiers of microcapillary electrophoresis traces. Nucleic Acids Research, 33(6), e56.
Publication 2005
Adult Biological Assay BLOOD Brain Breast Cell Lines cesium chloride Colon DNA Chips DNA Replication Electrophoresis Endoribonucleases Epithelium Histocompatibility Testing Homo sapiens isolation Kidney Liver Lung Lymphoma Muscle Tissue Phenols Promega Prostate Rectum Silica Gel Thyroid Gland Tissues trizol Ultracentrifugation

Most recents protocols related to «Silica Gel»

1
Synthesis of Pyrrolidine Derivatives
Not available on PMC !

Example 26

[Figure (not displayed)]

Synthesis of 169-A.

A mixture of tert-butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (750 mg, 3.54 mmol), 1-methylpiperidin-4-one (800 mg, 7.08 mmol) and acetic acid (2 drops) in DCE (15 mL) was stirred at 50° C. for 2 h. Then Sodium triacetoxyborohydride (1.50 g, 7.08 mmol) was added into above mixture and stirred at 50° C. for another 2 h. After the reaction was completed according to LCMS, the solvent was diluted with water (10 mL) and then extracted by DCM (10 mL×3). The combined organics washed with brine (10 mL×3), dried over anhydrous Na2SO4 and then concentrated in vacuo. The residue was purified by column chromatography on silica gel (DCM:MeOH=100:1˜50:1) to give 169-A (750 mg, 69%) as a yellow oil.

Synthesis of 169-B.

A solution of 169-A (400 mg, 1.29 mmol) in DCM (10 mL) was added TFA (5 mL) and stirred at room temperature for 1 h. when LCMS showed the reaction was finished. The solvent was removed in vacuo to give 169-B as a crude product and used to next step directly.

Synthesis of 169-C.

A mixture of 143-C (306 mg, 0.65 mmol) and 169-B (crude product from last step) in acetonitrile (6 mL) was stirred at 50° C. for 30 min. Then Na2CO3 (624 mg, 6.50 mmol) was added into above mixture and stirred at 50° C. for 3 h. After the reaction was completed according to LCMS, the mixture was cooled to room temperature. The Na2CO3 was removed by filtered. The filtrate was concentrated in vacuo. The residue was purified by column chromatography on silica gel (DCM:MeOH=100:1˜20:1) to give 169-C (230 mg, 76%) as a yellow solid.

Synthesis of 169.

A mixture of 169-C (230 mg, 0.49 mmol) and Pd/C (230 mg) in MeOH (10 mL) was stirred at room temperature for 30 min under H2 atmosphere. Pd/C was then removed by filtration through the Celite. The filtrate was concentrated and the residue was purified by Pre-TLC (DCM:MeOH=10:1) to give 169 (150 mg, 70%) as a white solid.

Compounds 152, 182, 199, 201, 202, 203, 235, 236 and 256 were synthesized in a similar manner using the appropriately substituted aldehyde or ketone variant of 169.

Compound 152.

50 mg, 36%, a light yellow solid.

Compound 182.

70 mg, 38%, a red solid.

Compound 199.

50 mg, 54%, a light yellow solid.

Compound 201.

30 mg, 42%, as a yellow solid.

Compound 202.

30 mg, 42%, a yellow solid.

Compound 203.

30 mg, 18%, a yellow solid.

Compound 235.

170 mg, 87%, a white solid.

Compound 236.

70 mg, 50%, a white solid.

Compound 256.

20 mg, 8%, a light yellow solid.

Compounds 210, 211, 215, 222, 223, 242 and 262 were synthesized in a similar manner using the appropriately substituted amine variant of 169.

Compound 210.

160 mg, 96%, a tan solid.

Compound 211.

70 mg, 40%, a white solid

Compound 215.

70 mg, 75%, a white solid.

Compound 222.

30 mg, 42%, a yellow solid.

Compound 223.

35 mg, 31%, a white solid.

Compound 242.

50 mg, 34%, a white solid.

Compound 262.

38 mg, 43%, a white solid.

US11858939B2. Hetero-halo inhibitors of histone deacetylase (2024-01-02). Alkermes, Inc. [US]. Inventors: Martin R. Jefson [US], John A. Lowe, III [US], Fabian Dey [CH], Andreas Bergmann [DE], Andreas Schoop [DE], Nathan Oliver Fuller [US].
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Patent 2024
Acetic Acid acetonitrile Aldehydes Amines Anabolism Atmosphere brine Celite Chromatography compound 26 compound 235 Filtration Ketones Light Lincomycin Pyrrole Silica Gel Sodium Solvents TERT protein, human
2
Synthesis of Pyrido[3,4-b]pyrazine Derivative
Not available on PMC !

Example 11

[Figure (not displayed)]

Step a: To a stirred suspension of 2,4-dichloro-6-methyl-3-nitropyridine (2.5 g, 12 mmol) in 24 mL of THE was added a solution of 7N NH3 in MeOH (14 mL, 98 mmol). After stirring for 3 h, the volatiles were removed in vacuo. The crude residue was purified by silica gel column chromatography to give 2-chloro-6-methyl-3-nitropyridin-4-amine. C6H7CN3O2 [M+H]+ 188.0, found 188.0.

Step b: To a stirred mixture of 2-chloro-6-methyl-3-nitropyridin-4-amine (760 mg, 4.1 mmol) and Fe (1.1 g, 20 mmol) in a 5:1 solution of EtOH/H2O (24 mL) was added 4.4 mL of conc. HCl. The contents were refluxed for 30 min, then cooled to room temperature and quenched with 100 mL of sat. NaHCO3 (aq). The mixture was extracted with EtOAc and the combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to yield 2-chloro-6-methylpyridine-3,4-diamine. MS: (ES) m/z calculated for C6H9ClN3 [M+H]+ 158.0, found 158.0.

Step c: To a stirred solution of 2-chloro-6-methylpyridine-3,4-diamine (0.49 g, 3.1 mmol) in 3 mL of EtOH was added a 40% w/w aqueous solution of glyoxal (2.0 mL, 12 mmol). After refluxing for 16 h, the mixture was diluted with H2O and extracted with EtOAc. The organic layers were combined, dried over MgSO4, filtered and concentrated in vacuo. The crude residue was purified by silica gel column chromatography to give 5-chloro-7-methylpyrido[3,4-b]pyrazine. MS: (ES) m/z calculated for C8H7ClN3 [M+H]+ 180.0, found 180.1.

Step d: To a stirred solution of 5-chloro-7-methylpyrido[3,4-b]pyrazine (200 mg, 1.0 mmol) and 2′-chloro-2-methyl-3′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1′-biphenyl]-3-amine (350 mg, 1.0 mmol) in 2 mL of MeCN was added AcOH (0.18 mL, 3.1 mmol). After 30 min, the volatiles were concentrated in vacuo. The crude residue was purified by silica gel column chromatography to give N-(2′-chloro-2-methyl-3′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1′-biphenyl]-3-yl)-7-methylpyrido[3,4-b]pyrazin-5-amine. MS: (ES) m/z calculated for C27H29BClN4O2 [M+H]+ 487.2, found 487.2.

Step e: To a stirred solution of N-(2′-chloro-2-methyl-3′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1′-biphenyl]-3-yl)-7-methylpyrido[3,4-b]pyrazin-5-amine (390 mg, 0.66 mmol), 6-chloro-2-methoxynicotinaldehyde (240 mg, 1.4 mmol), and K3PO4 (490 mg, 2.3 mmol) in a 1:1 solution of 1,4-dioxane/H2O (3.3 mL) under N2 (g) was added Pd(PPh3)4 (76 mg, 0.066 mmol). The mixture was stirred under N2 (g) at 90° C. for 3 h. The mixture was diluted with H2O and then extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated. The crude residue was purified by silica gel column chromatography to give 6-(2-chloro-2′-methyl-3′-((7-methylpyrido[3,4-b]pyrazin-5-yl)amino)-[1,1′-biphenyl]-3-yl)-2-methoxynicotinaldehyde. MS: (ES) m/z calculated for C28H23ClN5O2 [M+H]+ 496.2, found 496.2.

Step f: To a stirred mixture of 6-(2-chloro-2′-methyl-3′-((7-methylpyrido[3,4-b]pyrazin-5-yl)amino)-[1,1′-biphenyl]-3-yl)-2-methoxynicotinaldehyde (120 mg, 0.25 mmol), (S)-5-(aminomethyl)pyrrolidin-2-one hydrochloride (150 mg, 0.99 mmol), and trimethylamine (0.14 mL, 0.99 mmol) in a 4:1 solution of DCM/MeOH (5 mL) was added NaBH(OAc)3 (530 mg, 2.5 mmol). After stirring for 30 min, the mixture was filtered through Celite, and the filtrate was concentrated in vacuo. The product was purified by preparative HPLC to give the product (S)-5-((((6-(2-chloro-2′-methyl-3′-((7-methylpyrido[3,4-b]pyrazin-5-yl)amino)-[1,1′-biphenyl]-3-yl)-2-hydroxypyridin-3-yl)methyl)amino)methyl)pyrrolidin-2-one. 1H NMR (400 MHz, DMSO-d6) δ 12.59 (s, 1H), 9.32 (s, 1H), 9.07 (d, J=2.0 Hz, 1H), 8.86 (d, J=2.0 Hz, 1H), 8.23 (d, J=8.7 Hz, 1H), 7.76 (d, J=7.0 Hz, 1H), 7.62 (s, 1H), 7.55 (d, J=7.5 Hz, 1H), 7.50-7.43 (m, 1H), 7.35 (dd, J=7.9, 7.9 Hz, 1H), 7.12 (s, 1H), 6.96 (d, J=7.5 Hz, 1H), 6.55 (s, 2H), 6.43 (d, J=7.1 Hz, 1H), 4.07 (s, 3H), 3.95-3.84 (m, 1H), 2.48 (s, 4H), 2.26-2.15 (m, 3H), 2.11 (s, 3H), 1.86-1.70 (m, 1H). MS: (ES) m/z calculated for C32H31ClN7O2 [M+H]+ 580.2, found 580.1.

US11866429B2. Heteroaryl-biphenyl amines for the treatment of PD-L1 diseases (2024-01-09). CHEMOCENTRYX, INC. [US]. Inventors: Pingchen Fan [US], Christopher W. Lange [US], Rebecca M. Lui [US], Darren J. McMurtrie [US], Ryan J. Scamp [US], Ju Yang [US], Yibin Zeng [US], Penglie Zhang [US].
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Patent 2024
1H NMR 2-picoline 4-nitropyridine Amines Bicarbonate, Sodium Celite Chromatography Diamines Dioxanes diphenyl Ethanol Gel Chromatography Glyoxal High-Performance Liquid Chromatographies Pyrazines Silica Gel Silicon Dioxide Sulfate, Magnesium Sulfoxide, Dimethyl trimethylamine
3
Synthesis of Triazolopyrimidine Derivatives
Not available on PMC !

Example 2

[Figure (not displayed)]

N-(2-chloro-4-(trifluoromethyl)phenyl)-2-(5-ethyl-2-morpholino-7-oxo-6-(piperazin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-4(7H)-yl)acetamide (Intermediate B) (200 mg, 352 μmol) was suspended in DMF (5 mL). Perfluorophenyl 3-hydroxypicolinate (Intermediate CT) (215 mg, 703 μmol) and Et3N (97.0 μL, 703 μmol) were added and the RM was stirred at 70° C. for 3 hours. The RM was concentrated under reduced pressure. The crude product was first purified by column chromatography (Silica gel column: Silica 12 g, eluent DCM:MeOH 100:0 to 90:10). Then a second purification by reverse phase preparative HPLC (RP-HPLC acidic 9: 40 to 50% B in 2 min, 50 to 55% B in 10 min) afforded the title compound.

LC-MS: Rt=0.98 min; MS m/z [M+H]+ 690.6/692.6, m/z [M−H]− 688.4/690.3; UPLC-MS 1

LC-MS: Rt=4.84 min; MS m/z [M+H]+ 690.2/692.2 m/z [M−H]− 688.3/690.3; UPLC-MS 2

1H NMR (400 MHz, DMSO-d6) δ 10.37 (s, br, 1H), 10.34 (s, br, 1H), 8.05 (m, 2H), 7.96 (d, J=2.1 Hz, 1H), 7.72 (dd, J=2.1 Hz, 8.7 Hz, 1H), 7.28 (m, 2H), 5.21 (s, 2H), 4.53 (m, 1H), 3.66 (m, 4H), 3.46 (m, 3H), 3.38 (m, 4H), 3.20 (m, 1H), 2.92 (m, 3H), 2.76 (m, 1H), 2.58 (m, 1H), 1.16 (t, J=7.5 Hz, 3H)

Example 24

[Figure (not displayed)]

To the stirred solution of N-(2-chloro-6-(trifluoromethyl)pyridin-3-yl)-2-(5-ethyl-2-(4-methoxycyclohex-1-en-1-yl)-7-oxo-6-(piperazin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-4(7H)-yl)acetamide (Intermediate Y) (300 mg, 504 μmol), 4-chloro-3-hydroxypicolinic acid (140 mg, 807 μmol), HOBt (136 mg, 1.01 mmol) and EDC.HCl (193 mg, 1.01 mmol) in DCM (20 mL) was added pyridine (122 μL, 1.51 mmol) at 0° C. The RM was stirred at RT for 16 hours. The RM was quenched with NaHCO3 and extracted with DCM. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography (Silica gel column: Silica 4 g, eluent DCM:MeOH 100:0 to 98:2). The residue was purified by preparative chiral HPLC (instrument: Agilent 1200 series, with single quad mass spectrometer; column: LUX CELLULOSE-4, 250 mm×21.1 mm, 5.0 μm; eluent: A=hexane, B=0.1% HCOOH in EtOH; flow rate: 15 mL/min; detection: 210 nm; injection volume: 0.9 mL; gradient: isocratic: 50(A):50(B)).

Example 24a: The product containing fractions were concentrated at 40° C. and washed with n-pentane (5×10 mL), decanted and dried to give the title compound as an off-white solid—first eluting stereoisomer.

Chiral HPLC (C-HPLC 2): Rt=10.764 min

LC-MS: Rt=1.08 min; MS m/z [M+H]+ 750.5/752.5, m/z [M−H]− 748.4/750.4; UPLC-MS 1

LC-MS: Rt=5.29 min; MS m/z [M+H]+ 750.2/752.2, m/z [M−H]− 748.2/750.2; UPLC-MS 2

1H NMR (400 MHz, DMSO-d6) δ 10.68 (s, br, 2H), 8.56 (d, J=8.1 Hz, 1H), 7.98 (d, J=5.6 Hz, 1H), 7.94 (d, J=8.1 Hz, 1H), 7.50 (d, J=5.1 Hz, 1H), 6.72 (m, 1H), 5.34 (s, 2H), 4.53 (m, 1H), 3.52 (m, 4H), 3.28 (m, 4H), 2.98 (m, 3H), 2.80 (m, 1H), 2.63 (m, 1H), 2.55 (m, 1H), 2.46 (m, 1H), 2.16 (m, 2H), 1.95 (m, 1H), 1.68 (m, 1H), 1.17 (t, J=7.3 Hz, 3H)

Example 24b: The product containing fractions were concentrated at 40° C. and washed with n-pentane (5×10 mL), decanted and dried to give the title compound as an off-white solid—second eluting stereoisomer.

Chiral HPLC (C-HPLC 2): Rt=18.800 min

LC-MS: Rt=1.08 min; MS m/z [M+H]+ 750.1/752.1, m/z [M−H]− 748.2/750.2; UPLC-MS 1

LC-MS: Rt=5.30 min; MS m/z [M+H]+ 750.1/752.1, m/z [M−H]− 748.2/750.2; UPLC-MS 2

1H NMR (400 MHz, DMSO-d6) δ 10.83 (s, br, 1H), 10.55 (s, br, 1H), 8.56 (d, J=8.2 Hz, 1H), 8.06 (d, J=5.3 Hz, 1H), 7.92 (d, J=8.2 Hz, 1H), 7.55 (d, J=5.3 Hz, 1H), 6.72 (m, 1H), 5.35 (s, 2H), 4.54 (m, 1H), 3.54 (m, 4H), 3.28 (m, 3H), 3.25 (m, 1H), 2.99 (m, 3H), 2.81 (m, 1H), 2.62 (m, 1H), 2.41 (m, 2H), 2.16 (m, 2H), 1.96 (m, 1H), 1.66 (m, 1H), 1.18 (t, J=7.3 Hz, 3H)

Example 25

[Figure (not displayed)]

N-(2-chloro-6-(trifluoromethyl)pyridin-3-yl)-2-(5-ethyl-2-(4-methoxycyclohex-1-en-1-yl)-7-oxo-6-(piperazin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidin-4(7H)-yl)acetamide.HCl (Intermediate Y) (120 mg, 190 μmol) and DIPEA (166 μL, 950 μmol) were dissolved in DCM (5 mL) and then 3-hydroxypicolinoyl chloride (Intermediate CV) (59.9 mg, 380 μmol) was added at 0° C. and stirred for 2 hours. 3-hydroxypicolinoyl chloride (Intermediate CV) (59.9 mg, 380 μmol) was added again and the reaction was continued under stirring for 12 hours. The RM was diluted with DCM and washed with water and aq NaHCO3 (2×20 mL), washed with water and brine, dried over Na2SO4, filtered and concentrated. The crude product was combined with another experiment and purified by column chromatography (Silica gel column: Silica 4 g, eluent DCM:MeOH 100:0 to 99:1) then further purified by reverse phase preparative HPLC (RP-HPLC acidic 10: 40 to 50% B in 2 min, 50 to 60% B in 8 min) to give the title compound as an off-white solid.

The racemate was purified by preparative chiral HPLC (instrument: Agilent 1200 series, with single quad mass spectrometer; column: CELLULOSE-4, 250 mm×21.2 mm; eluent: A=hexane, B=0.1% HCOOH in MeOH:EtOH 1:1; flow rate: 20 mL/min; detection: 210 nm; injection volume: 0.9 mL; gradient: isocratic 60(A):40(B)).

Example 25a: First eluting stereoisomer, off-white solid.

Chiral HPLC (C-HPLC 1): Rt=10.070 min

LC-MS: Rt=0.98 min; MS m/z [M+H]+ 716.5/718.6, m/z [M−H]− 714.3/716.3; UPLC-MS 1

LC-MS: Rt=4.76 min; MS m/z [M+H]+ 716.2/718.2, m/z [M−H]− 714.2/716.2; UPLC-MS 2

1H NMR (400 MHz, DMSO-d6) δ 10.46 (s, br, 2H), 8.56 (d, J=8.5 Hz, 1H), 8.05 (m, 1H), 7.90 (d, J=8.4 Hz, 1H), 7.28 (m, 2H), 6.72 (m, 1H), 5.30 (s, 2H), 4.54 (m, 1H), 3.47 (m, 4H), 3.27 (s, 3H), 3.21 (m, 1H), 2.96 (m, 3H), 2.79 (m, 1H), 2.59 (m, 3H), 2.43 (m, 1H), 2.14 (m, 1H), 1.95 (m, 1H), 1.67 (m, 1H), 1.17 (t, J=7.2 Hz, 3H)

Example 25b: Second eluting stereoisomer, off-white solid.

Chiral HPLC (C-HPLC 1): Rt=16.023 min

LC-MS: Rt=0.96 min; MS m/z [M+H]+ 716.3/718.3, m/z [M−H]− 714.3/716.3; UPLC-MS 1

LC-MS: Rt=4.77 min; MS m/z [M+H]+ 716.2/718.2, m/z [M−H]− 714.2/716.2; UPLC-MS 2

1H NMR (400 MHz, DMSO-d6) δ 10.39 (s, br, 2H), 8.56 (d, J=8.0 Hz, 1H), 8.06 (m, 1H), 7.93 (d, J=8.1 Hz, 1H), 7.28 (m, 2H), 6.72 (m, 1H), 5.32 (s, 2H), 4.54 (m, 1H), 3.46 (m, 4H), 3.27 (s, 3H), 3.20 (m, 1H), 2.96 (m, 3H), 2.79 (m, 1H), 2.59 (m, 3H), 2.41 (m, 1H), 2.14 (m, 1H), 1.95 (m, 1H), 1.68 (m, 1H), 1.17 (t, J=7.1 Hz, 3H)

US11878973B2. Bicyclic compounds and their uses (2024-01-23). NOVARTIS AG [CH]. Inventors: Vincent Bordas [FR], Jvan Brun [CH], Markus Furegati [CH], Jacques Hamon [FR], Jürgen Hans-Hermann Hinrichs [DE], Philipp Holzer [CH], Fatma Limam [FR], Henrik Möbitz [DE], Sandro Nocito [CH], Simone Plattner [DE], Niko Schmiedeberg [CH], Joseph Schoepfer [CH], Ross Sinclair Strang [FR], Frédéric Zecri [US].
Full text: Click here
Patent 2024
1-hydroxybenzotriazole 1H NMR acetamide Acids Bicarbonate, Sodium Bicyclo Compounds brine Cellulose Chlorides Chromatography DIPEA Ethanol H 718 Hexanes High-Performance Liquid Chromatographies Morpholinos pentane Piperazine Pressure pyridine Silica Gel Silicon Dioxide Stereoisomers Sulfoxide, Dimethyl Tandem Mass Spectrometry
4
Synthesis of Fluorescent Labeling Probe
Not available on PMC !

Example 125

[Figure (not displayed)]

Methyl 4-((5-(benzyloxy)-2-methoxyphenyl)(ethyl)amino)butanoate (184). 5-(Benzyloxy)-N-ethyl-2-methoxyaniline (146) (0.681 g, 2.65 mmol), DIEA (0.92 mL, 5.3 mmol), and methyl 4-iodobutyrate (0.72 mL, 5.3 mmol) in DMF (5 mL) were stirred at 70° C. for 5 days. The reaction mixture was cooled to rt, diluted with EtOAc (60 mL), washed with water (4×50 mL), brine (75 mL), dried over Na2SO4 and evaporated. The residue was purified by chromatography on a silica gel column (2.5×30 cm bed, packed with CHCl3), eluant: 5% MeOH in CHCl3 to get compound 184 (0.72 g, 76%) as a dark amber oil.

Methyl 4-(ethyl(5-hydroxy-2-methoxyphenyl)amino)butanoate (186). Ester 184 (0.72 g, 2.0 mmol) was stirred under reflux with 6 mL of water and 6 mL of conc HCl for 1.5 hrs and then evaporated to dryness to give acid 185 as a brown gum. The crude acid was dissolved in 50 mL of methanol containing 1 drop (cat.) of methanesulfonic acid ant the solution was kept for 2 hrs at rt. After that the mixture was concentrated in vacuum and the residue was mixed with 20 mL of saturated NaHCO3. The product was extracted with EtOAc (3×40 mL). The extract was washed with brine (40 mL), dried over Na2SO4 and evaporated. The residue was purified by chromatography on a silica gel column (2.5×30 cm bed, packed with CHCl3), eluant: 5% MeOH in CHCl3 to get compound 186 (0.444 g, 83%) as a brown oil.

N-(6-(dimethylamino)-9-(4-(ethyl(4-methoxy-4-oxobutyl)amino)-2-hydroxy-5-methoxyphenyl)-3H-xanthen-3-ylidene)-N-methylmethanaminium chloride (187). To a stirred suspension of tetramethylrhodamine ketone 101 (0.234 g, 0.830 mmol) in 10 mL of dry chloroform was added oxalyl chloride (72 μL, 0.82 mmol) upon cooling to 0-5° C. The resulting red solution was stirred for 0.5 h at 5° C., and the solution of compound 186 (0.222 g, 0.831 mmol) in dry chloroform (5 mL) was introduced. The reaction was allowed to heat to rt, stirred for 72 h, diluted with CHCl3 (100 mL and washed with sat. NaHCO3 solution (2×30 mL) The organic layer was extracted with 5% HCl (3×25 mL). The combined acid extract was washed with CHCl3 (2×15 mL; discarded), saturated with sodium acetate and extracted with CHCl3 (5×30 mL). The extract was washed with brine (50 mL), dried over Na2SO4 and evaporated. The crude product was purified by chromatography on silica gel column (2×50 cm bed, packed with CHCl3/MeOH/AcOH/H2O (100:20:5:1)), eluant: CHCl3/MeOH/AcOH/H2O (100:20:5:1) to give the product 187 (0.138 g, 29%) as a purple solid.

4-((4-(6-(dimethylamino)-3-(dimethyliminio)-3H-xanthen-9-yl)-5-hydroxy-2-methoxyphenyl)(ethyl)amino)butanoate (188). Methyl ester 187 (0.136 g, 0.240 mmol) was dissolved in 5 mL of 1M KOH (5 mmol). The reaction mixture was kept at rt for 1.5 hrs and the acetic acid (1 mL) was added. The mixture was extracted with CHCl3 (4×30 mL), and combined extract was washed with brine (20 mL), filtered through the paper filter and. The crude product was purified by chromatography on silica gel column (2×50 cm bed, packed with MeCN/H2O (4:1)), eluant: MeCN/H2O/AcOH/(4:1:1) to give the product 188 (0.069 g, 98%) as a purple solid.

N-(6-(dimethylamino)-9-(4-((4-(2,5-dioxopyrrolidin-1-yloxy)-4-oxobutyl)(ethyl)amino)-2-hydroxy-5-methoxyphenyl)-3H-xanthen-3-ylidene)-N-methylmethanaminium chloride (189). To a solution of the acid 188 (69 mg, 0.12 mmol) in DMF (2 mL) and DIEA (58 μL, 0.33 mmol) was added N-hydroxysuccinimide trifluoroacetate (70 mg, 0.33 mmol). The reaction mixture was stirred for 30 min, diluted with chloroform (100 mL) and washed with water (5×50 mL), brine (50 mL), filtered through paper and concentrated in vacuum. The crude product was purified by precipitation from CHCl3 solution (5 mL) with ether (20 mL) to give compound 189 (55 mg, 67%) as a purple powder.

US11867698B2. Fluorogenic pH sensitive dyes and their method of use (2024-01-09). Life Technologies Corporation [US]. Inventors: Jeffrey Dzubay [US], Kyle Gee [US], Vladimir Martin [US], Aleksey Rukavishnikov [US], Daniel Beacham [US].
Full text: Click here
Patent 2024
Acetic Acid Acids Amber Anabolism Bicarbonate, Sodium brine Chlorides Chloroform Chromatography Esters Ethyl Ether Hydroxyl Radical Ketones methanesulfonic acid Methanol N,N-diisopropylethylamine N-hydroxysuccinimide oxalyl chloride Powder Silica Gel Sodium Acetate tetramethylrhodamine Trifluoroacetate Vacuum
5
Synthesis of 7-Chloro-4-(1H-imidazol-1-yl)-8-methylquinoline Derivatives
Not available on PMC !

Example 54

[Figure (not displayed)]

4,7-Dichloro-8-methylquinoline (53 mg, 0.25 mmol), imidazole (43 mg, 0.63 mmol), potassium t-butoxide (42 mg, 0.38 mmol), Bis(triphenylphosphine)palladium(II) dichloride (9 mg, 0.013 mmol) and DMF (3 mL) were placed in a vial under N2. The mixture was heated at 110° C. for 2 h. After cooling down to room temperature, the crude is diluted by EtOAc (20 mL) and washed by water (5 mL×2) and brine (5 mL×2). The organic phase is concentrated and purified by column chromatography on silica gel to give 7-chloro-4-(1H-imidazol-1-yl)-8-methylquinoline as a solid. (MS: [M+1]+ 244.0)

The following compounds are prepared essentially by the same method described above to prepare I-421.

MS
I-#Starting MaterialStructure[M + 1]+
I-422[Figure (not displayed)]
[Figure (not displayed)]
[Figure (not displayed)]
298

US11873291B2. Quinoline cGAS antagonist compounds (2024-01-16). ImmuneSensor Therapeutics, Inc. [US], The Board of Regents of the University of Texas System [US]. Inventors: Jian Qiu [US], Qi Wei [US], Matt Tschantz [US], Heping Shi [US], Youtong Wu [US], Hulling Tan [US], Lijun Sun [US], Chuo Chen [US], Zhijian Chen [US].
Full text: Click here
Patent 2024
8-methylquinoline Anabolism brine Chromatography imidazole Palladium Potassium Silica Gel triphenylphosphine

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