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Oil, Mineral

Oil and mineral resources are critical components of modern society, powering industries, fueling transportation, and providing raw materials for a wide range of products.
This MeSH term encompasses the study of the geological formation, extraction, and utilization of these natural resources, including petroleum, natural gas, coal, metallic ores, and industrial minerals.
Researchers in this field investigate exploration techniques, production methods, environmental impacts, and economic factors to optimize the sustainable management of oil and mineral assets.
The PubCompare.ai platform leverages advanced AI to streamline this research, helping scientists easily identify the most effective protocols and products to accelerate their work and address the world's growing energy and resource needs.

Most cited protocols related to «Oil, Mineral»

1
Efficient Electroporation and Cryopreservation of Mouse ES Cells
Cited 173 times
The final targeting constructs were prepared for ES cell electroporation from 2 ml of culture (2X LB plus antibiotics) in 96-well format using the Qiagen Turboprep kit. Before electroporation, vectors were linearized with AsiSI and examined by gel electrophoresis. For most clones, the digested DNA migrated as a single high-molecular-mass band of the expected size (Supplementary Fig. 5). Occasionally, contaminating smaller molecular mass bands were also observed on the gel (DNA quality failures).
JM8 mouse ES cell lines derived from the C57BL/6N strain were grown either on a feeder layer of SNL6/7 fibroblasts (neomycin and/or puromycin resistant) or on gelatinized tissue culture plates16 (link). Both feeder-independent and feeder-dependent lines were maintained in Knockout DMEM (500 ml, Gibco) supplemented with 2 mM glutamine, 5 ml 100× β-mercaptoethanol (360 μl in 500 ml PBS, filter sterilized), 10–15% fetal calf serum respectively (Invitrogen) and 500 U ml−1 leukaemia-inhibitory factor (ESGRO, Millipore). Trypsin solution was prepared by adding 20 ml of 2.5% trypsin solution (Gibco) and 5 ml chicken serum (Gibco) to 500 ml filter-sterilized PBS containing 0.1 g EDTA (Sigma) and 0.5 g d-glucose (Sigma).
Electroporations of ES cells were carried out in a 25-well cuvette using the ECM 630 96-well electroporator /HT-200 automatic plate handler (BTX Harvard Apparatus; set at 700 V, 400 Ω, 25 μF). Immediately before electroporation, cell suspensions of ~1 × 107 cells and ~2 μg of linearized targeting vector DNA were mixed in a final volume of 120 μl PBS. Cells were seeded onto a 10-cm dish (with feeders or gelatin) and colonies were picked after 10 d of selection in 100 μg (active) per ml Geneticin (Invitrogen). To expand cells into duplicate wells for archiving and preparation of genomic DNA, confluent cultures of JM8 ES cells grown on feeder cells were washed twice with pre-warmed PBS and trypsinized for 15 min at 37 °C. Five volumes of pre-warmed media were added and the cells were gently dispersed by tituration and passed at a dilution of 1:4 into new plates containing feeder cells. Passage of cells grown on gelatinized plates was carried out in a similar manner except that the cells were trypsinized for 10 min and passed at a dilution of 1:6 into freshly gelatin-coated plates (0.1% gelatin, Sigma G1393). Culture medium was replaced daily and cells reached confluence 2 days after passage. To archive ES cell clones, trypsinized cells from confluent 96-well plates were transferred in 200 μl freezing medium (Knockout DMEM, 15% serum/ 10% DMSO) to 96-well cryovials (Matrix) and overlayed with sterile mineral oil. The cells were placed at −80 °C overnight and then transferred to liquid nitrogen.
Skarnes W.C., Rosen B., West A.P., Koutsourakis M., Bushell W., Iyer V., Mujica A.O., Thomas M., Harrow J., Cox T., Jackson D., Severin J., Biggs P., Fu J., Nefedov M., de Jong P.J., Stewart A.F, & Bradley A. (2011). A conditional knockout resource for the genome–wide study of mouse gene function. Nature, 474(7351), 337-342.
Publication 2011
2-Mercaptoethanol Antibiotics Cells Chickens Clone Cells Cloning Vectors Edetic Acid Electrophoresis Electroporation Embryonic Stem Cells Feeder Cell Layers Feeder Cells Fetal Bovine Serum Fibroblasts Gelatins Geneticin Genome Glucose Glutamine Hyperostosis, Diffuse Idiopathic Skeletal LIF protein, human Mus Neomycin Nitrogen Oil, Mineral PRSS2 protein, human Puromycin Serum Sterility, Reproductive Strains Sulfoxide, Dimethyl Technique, Dilution Tissues Trypsin
2
Visualizing Cortical Circuits in Awake Mice
Cited 20 times
All procedures were approved by the Janelia Farm Research Campus Institutional Animal Care and Use Committee. We used adult (> P60) male PV-IRES-cre mice (B6;129P2-Pvalbtm1(cre)Arbr/J, The Jackson Laboratory). All surgeries were conducted under isoflurane anesthesia (1.5–2%). Additional drugs reduced potential inflammation (Ketofen, 5mg/kg, subcutaneously) and provided local (Marcaine, 0.5% solution injected under the scalp) and general analgesia (Buprenorphine, 0.1 mg/kg, intraperitoneal). A circular piece of scalp was removed and the underlying bone was cleaned and dried. The periostium was removed with a dental drill and the exposed skull was covered with a thin layer of cyano-acrylic primer (Crazy glue). A custom-machined titanium frame was cemented to the skull with dental acrylic (Lang Dental).
Afferents from the somatosensory cortex were labeled with virus expressing tdTomato 33 (rAAV-CAG-tdTomato, serotype 2/1; 20 nl at 300 and 550 um depths). The C2 barrel was targeted based on intrinsic signal imaging 28 (link). The virus was injected with a custom, piston-based, volumetric injection system (based on a Narishige, MO-10, manipulator) 46 (link). Glass pipettes (Drummond) were pulled and beveled to a sharp tip (30 um outer diameter). Pipettes were back-filled with mineral oil and front-loaded with viral suspension immediately prior to injection.
A craniotomy was made over vM1 (size, 3×2mm; center relative to Bregma: lateral, 0.8 mm; anterior, 1 mm, left hemisphere, Fig. 2a–d). These coordinates were previously determined using intracortical microstimulation 8 (link),16 (link),18 (link), mapping axonal projections from vS1 in vM1 8 (link),47 (link), and trans-cellular labeling with pseudorabies virus (data not shown). Neurons underlying the craniotomy were labeled by injecting virus expressing GCamP3 (rAAV-syn-GCaMP3, serotype 2/1, produced by the University of Pennsylvania Gene Therapy Program Vector Core). The brain was covered with agar (2%). 4–8 sites (10–15 nl/site; depth, 150–210 um; rate, 10 nl/minute) were injected per craniotomy.
The imaging window was constructed from two layers of standard microscope coverglass (Fisher; # 2, thickness, 170 – 210 um), joined with a UV curable optical glue (NOR-61, Norland): a larger piece was attached to the bone; a smaller insert fit snugly into the craniotomy (Fig. 2b, d). The bone surrounding the craniotomy was thinned to allow for a flush fit between insert and the underlying dura.
After virus injection, the glass window was lowered into the craniotomy. The space between the glass and the bone was sealed off with a thin layer of agar (2%), and the window was cemented in place using dental acrylic (Lang Dental). At the end of the surgery, all whiskers on the right side of the snout except row C were trimmed. The mice recovered for 3 days before starting water restriction. Imaging sessions started 14–21 days after the surgery.
Huber D., Gutnisky D.A., Peron S., O’Connor D.H., Wiegert J.S., Tian L., Oertner G., Looger L.L, & Svoboda K. (2012). Multiple dynamic representations in the motor cortex during sensorimotor learning. Nature, 484(7395), 473-478.
Publication 2012
Adult Agar Axon Bones Brain Buprenorphine Cells Craniotomy Cranium Dental Anesthesia Dental Health Services Drill Dura Mater Flushing Genetic Vectors Inflammation Institutional Animal Care and Use Committees Internal Ribosome Entry Sites Isoflurane Males Management, Pain Marcaine Microscopy Mus Neurons Oil, Mineral Oligonucleotide Primers Operative Surgical Procedures Pharmaceutical Preparations Reading Frames Scalp Somatosensory Cortex Suid Herpesvirus 1 tdTomato Titanium Vibrissae Virus
3
Visualizing Mitochondrial Dynamics in Embryonic Cells
Cited 20 times
MEFs were derived from e10.5 embryos. Embryos were mechanically dispersed by repeated passage through a P1000 pipette tip and plated with MEF media (DME, 10% FCS, 1× nonessential amino acids, 1 mM l-glutamine, penicillin/streptomycin [Life Technologies/GIBCO BRL]).
For visualization of mitochondria, the MEFs were either stained with 150 nM MitoTracker Red CMXRos (Molecular Probes) or infected with a retrovirus expressing EYFP fused to the presequence from subunit VIII of human cytochrome c oxidase, which directs EYFP to the mitochondrial matrix (a gift from R. Lansford, California Institute of Technology, Pasadena, CA) (Okada et al., 1999 (link)). To facilitate immortalization, the MEFs were later infected with a retrovirus expressing SV40 large T antigen (a gift from L. Jackson-Grusby, Massachusetts Institute of Technology) (Jat et al., 1986 (link)). Neither retroviral infection nor immortalization affected mitochondrial morphology. To label actin filaments, cells were fixed in 4% PFA and stained with 2.5 U/ml rhodamine-phalloidin (Molecular Probes). The stained cells were postfixed in 4% PFA.
For time-lapse confocal microscopy, cells were plated at low density onto chambered glass coverslips. Cells with culture medium were overlaid with light mineral oil and imaged in a 37°C chamber. EYFP-optimized filters and dichroics (q497lp, HQ500lp; Chroma) were used on a Zeiss 410 laser scanning confocal microscope (Carl Zeiss MicroImaging, Inc.)
TS cells from e3.5 blastocysts were derived using established protocols (Tanaka et al., 1998a (link)). Live cells were stained with MitoTracker Red (150 nM) and Syto16 (100 nM; Molecular Probes).
Chen H., Detmer S.A., Ewald A.J., Griffin E.E., Fraser S.E, & Chan D.C. (2003). Mitofusins Mfn1 and Mfn2 coordinately regulate mitochondrial fusion and are essential for embryonic development. The Journal of Cell Biology, 160(2), 189-200.
Publication 2003
Amino Acids Blastocyst Cell Culture Techniques Cells COX8C protein, human Culture Media Embryo Glutamine Large T-Antigen Light Microfilaments Microscopy, Confocal Mitochondria Mitochondrial Inheritance MitoTracker red CMXRos Molecular Probes Oil, Mineral Penicillins Retroviridae Retroviridae Infections rhodamine-phalloidin Simian virus 40 Streptomycin
4
Olfactory Deficit Screening in Mice
Cited 18 times
Mice were screened for olfactory deficits using an odor-cross habituation test (Fig 1A)(Sundberg et al., 1982 (link); Wilson and Linster, 2008 (link)). Odors (n=7; limonene, ethyl valerate, isoamyl acetate, pentanol, heptanone, propyl butyrate and nonane; Sigma Aldrich, St. Louis, MO) were diluted 1×10−3 in mineral oil and applied to a cotton-applicator stick which was then enclosed in a piece of odorless plastic tubing to prevent contact of the liquid odor with the testing chamber or animal yet still allow volatile odor delivery. Notably, such an odor presentation method controls for the influence of visual and/or somatosensory influences on odor investigation. Odors were delivered for 4 successive trials (1 block), 20sec each, separated by 30sec inter-trial intervals, by inserting the odor stick into a port on the side of the animal’s home cage (Fig 1A). Home cage testing was chosen over testing in a separate apparatus to minimize potential influences of stress and anxiety (due to the new environment/context) on the behavioral measures. Testing took place during the light phase of the animals’ (12:12) day: light cycle, over two daily sessions (3–4 odors/session) separated by 24–48 hrs. The duration of time spent investigating, defined as snout-oriented sniffing within 1cm of the odor presentation port, was recorded across all trials by a single observer blind to genotypes (D.W.W.). Home cages were cleaned with fresh corn cob bedding 24–48hrs prior to behavioral testing to reduce unnecessary background odors, yet still allowing for adaptation to the new bedding. The stainless steel food bin and water bottle were removed from cages immediately prior to testing.
Wesson D.W., Levy E., Nixon R.A, & Wilson D.A. (2010). Olfactory Dysfunction Correlates with Amyloid-β Burden in an Alzheimer's Disease Mouse Model. The Journal of Neuroscience, 30(2), 505-514.
Publication 2010
Acclimatization Animals Anxiety Butyrates ethyl valerate Food Genotype Gossypium isoamyl acetate Light Limonene Maize Mice, House nonane Obstetric Delivery Odors Oil, Mineral Sense of Smell Stainless Steel Visually Impaired Persons
5
Vitamin C and E for Preeclampsia Prevention
Cited 17 times
Eligible women who were no more than 15 weeks pregnant and who consented to participate in the study were given a supply of placebo and asked to return within 2 weeks. Those who returned, who had taken at least 50% of the placebo that they were supposed to have taken, and who still met the eligibility criteria were randomly assigned to receive capsules containing a combination of 1000 mg of vitamin C (ascorbic acid) and 400 IU of vitamin E (RRR-alpha-tocopherol acetate) or matching placebo (mineral oil). Both the vitamin and placebo capsules were manufactured by Strides, which had no role in the design of the study, the analysis or interpretation of the data, the preparation of the manuscript, or the decision to submit the manuscript for publication. The simple urn method, with stratification according to clinical center, was used by the data coordinating center to create a randomization sequence16 (link); boxes containing each participant’s supply of capsules were packaged according to this sequence. Neither the participants nor the investigators were aware of the treatment assignments.
Women were instructed to take the study drug each day until they delivered their babies. The study participants returned on a monthly basis to return any unused study drug from the previous month, receive a new supply of the study drug for the coming month, report on side effects, and have their blood pressure and urine protein level (as assessed on dipstick testing) measured. Clinical research staff also obtained data on neonatal and maternal outcomes at delivery.
To determine the primary outcome and the diagnosis of preeclampsia, deidentified medical charts of all women with pregnancy-associated hypertension were reviewed centrally by at least three reviewers who were unaware of the treatment assignments. All data were collected or abstracted by certified research personnel at the clinical centers and uploaded to a database that was managed by an independent data coordinating center, which was responsible for data analysis. The study was approved by the institutional review board at each clinical site and the data coordinating center. All participants provided written informed consent before enrollment.
Roberts J.M., Myatt L., Spong C.Y., Thom E.A., Hauth J.C., Leveno K.J., Pearson G.D., Wapner R.J., Varner M.W., Thorp JM J.r., Mercer B.M., Peaceman A.M., Ramin S.M., Carpenter M.W., Samuels P., Sciscione A., Harper M., Smith W.J., Saade G., Sorokin Y, & Anderson G.B. (2010). Vitamins C and E to Prevent Complications of Pregnancy-Associated Hypertension. The New England journal of medicine, 362(14), 1282-1291.
Publication 2010
alpha-Tocopherol Acetate Ascorbic Acid Blood Pressure Capsule Diagnosis Eligibility Determination Ethics Committees, Research Hypertension, Gestational Infant Infant, Newborn Mothers Obstetric Delivery Oil, Mineral Placebos Pre-Eclampsia Proteins Urine Vitamin E Vitamins Woman

Most recents protocols related to «Oil, Mineral»

1
Methylation of 15 to Afford 16
Not available on PMC !

Example 19

[Figure (not displayed)]

To a solution of 15 (408 g, 0.77 mol, 1.0 eq.) and methyl iodide (145 mL, 2.32 mol, 3.0 eq.) in THF (4 L) was added sodium hydride (60% dispersion in mineral oil, 62.2 g, 1.55 mol, 2.0 eq.) at 0° C. The resulting mixture was stirred at 0° C. overnight and then poured onto ice-water cooled saturated ammonium chloride (5 L) with vigorous stirring. The mixture was then extracted with EtOAc (3×500 mL) and the organic layers were dried, filtered, concentrated and purified by column chromatography with a gradient of 15-35% EtOAc in petroleum ether to afford product 16 (388 g, 93% yield) as a light yellow oil. 1H NMR (500 MHz, CDCl3) δ 8.09 (s, 1H), 4.95 (d, J=6.6 Hz, 1H), 4.41 (q, J=7.1 Hz, 2H), 3.56 (d, J=9.5 Hz, 1H), 2.98 (s, 3H), 2.27-2.06 (m, 4H), 1.83-1.70 (m, 2H), 1.41 (t, J=7.2 Hz, 3H), 1.29 (ddd, J=8.9, 6.8, 1.6 Hz, 3H), 1.01 (d, J=6.6 Hz, 3H), 0.96 (dt, J=8.0, 2.9 Hz, 15H), 0.92 (d, J=6.6 Hz, 3H), 0.90 (d, J=6.7 Hz, 3H). MS ESI m/z calcd for C25H46N5O4SSi [M+H]+ 540.30, found 540.30.

US11873281B2. Conjugates of cell binding molecules with cytotoxic agents (2024-01-16). HANGZHOU DAC BIOTECH CO., LTD. [CN], None [US], None [CN], None [CN]. Inventors: R. Yongxin Zhao [US], Yue Zhang [CN], Yourang Ma [CN].
Full text: Click here
Patent 2024
1H NMR Anabolism Chloride, Ammonium Chromatography Ice Light methyl iodide naphtha Oil, Mineral sodium hydride
2
Synthesis of Quinolinylated Diazepan Acetate
Not available on PMC !

Example 62

[Figure (not displayed)]

Step 1: tert-butyl 2-(4-(7-chloro-4-(1H-imidazol-1-yl)quinolin-2-yl)-2-oxo-1,4-diazepan-1-yl)acetate. To a solution of 4-(7-chloro-4-(1H-imidazol-1-yl)quinolin-2-yl)-1,4-diazepan-2-one (20 mg) and tert-butyl 2-bromoacetate (30 mg) in anhydrous DMF was added NaH (10 mg, 65% in mineral oil). After stirring 3 hours, the reaction mixture was diluted with EtOAc (10 mL) and carefully quenched with water (5 mL). Isolation of the organic layer and a column chromatography eluting with a gradient of hexanes and EtOAc afforded the desired intermediate tert-butyl 2-(4-(7-chloro-4-(1H-imidazol-1-yl)quinolin-2-yl)-2-oxo-1,4-diazepan-1-yl)acetate (20 mg) (MS: [M+1]+ 456).

Step 2: 2-(4-(7-chloro-4-(1H-imidazol-1-yl)quinolin-2-yl)-2-oxo-1,4-diazepan-1-yl)acetic acid. tert-butyl 2-(4-(7-chloro-4-(1H-imidazol-1-yl)quinolin-2-yl)-2-oxo-1,4-diazepan-1-yl)acetate was further treated with TFA (0.4 mL) in DCM (0.8 mL). Removal of DCM and TFA under reduced pressure and lyophilization afforded the desired product (10 mg)-2-(4-(7-chloro-4-(1H-imidazol-1-yl)quinolin-2-yl)-2-oxo-1,4-diazepan-1-yl)acetic acid (MS: [M+1]+ 400).

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
Acetate Acetic Acids Anabolism bromoacetate Chromatography Freeze Drying Hexanes imidazole isolation Oil, Mineral Pressure TERT protein, human
3
Synthesis of AM393-A from AM351-A
Not available on PMC !

Example 50

[Figure (not displayed)]

Synthesis of AM393-A.

To a cooled (0° C.) solution of NaH (190 mg, 50% in mineral oil, 4.0 mmol) in DMF (5 mL) was added AM351-A (400 mg, 1.6 mmol) and the mixture was stirred at room temperature for 20 min. The reaction mixture was cooled to 0° C. and methyl iodide was added. The reaction mixture was stirred with slow warming to room temperature for 1 h. The reaction mixture was quenched with ice-cold water (10 mL) and the product was extracted with DCM (20 mL×3). The combined organic layer was washed with brine (20 mL) and dried over anhydrous Na2SO4. The solvent was removed in vacuo and the residue was purified by column chromatography on silica gel (PE:EtOAc=90:10˜85:15) to give AM393-A (360 mg, 85%) as a yellowish gum.

Compound AM393 (120 mg, 99%, a grey solid) was synthesized in a similar procedure used for AM351 from AM351-I)

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].
Full text: Click here
Patent 2024
Anabolism brine Chromatography Cold Temperature Ice methyl iodide Oil, Mineral Silica Gel Solvents
4
Methyl Ether Synthesis via Alkylation of Piperidine Alcohol
Not available on PMC !

Example 219

[Figure (not displayed)]

Sodium hydride, 60% disp. in mineral oil (31 mg, 0.78 mmol) was added to 1-[trans-3-Hydroxy-4-(4-quinolin-3-yl-benzyl)-piperidin-1-yl]-propan-1-one (71 mg, 0.19 mmol) in THF (3.00 mL). After 5 min, methyl iodide (14.0 uL, 0.225 mmol) was added and the mixture was stirred at room temperature for 48 h. The mixture was concentrated in vacuo. The residue was dissolved in DCM, applied to a silica gel loading cartridge (5 g) and purified on silica gel (4 g, 10-100% ethyl acetate:hexane) to afford 1-[(trans)-3-methoxy-4-(4-quinolin-3-yl-benzyl)-piperidin-1-yl]-propan-1-one HCl (28 mg, 35%) after treatment of product containing fractions with HCl in dioxane and concentration. LCMS (ESI): 389 (M+H); 1H NMR (400 MHz, DMSO-d6) δ 9.24 (d, J=2.3 Hz, 1H) 8.62 (d, J=2.0 Hz, 1H) 8.00-8.14 (m, 2H) 7.73-7.83 (m, 3H) 7.60-7.69 (m, 1H) 7.35 (d, J=8.3 Hz, 2H) 4.14-4.42 (m, 1H) 3.76-3.97 (m, 1H) 3.39 (s, 3H) 3.10 (dd, J=13.6, 4.3 Hz, 1H) 2.69-2.96 (m, 3H) 2.50-2.56 (m, 1H) 2.30 (q, J=7.4 Hz, 2H) 1.77-1.92 (m, 1H) 1.55-1.70 (m, 1H) 1.08-1.22 (m, 1H) 1.00 (t, J=7.4 Hz, 3H);

US11878966B2. Substituted 4-benzyl and 4-benzoyl piperidine derivates (2024-01-23). 89BIO LTD [IL]. Inventors: Nadine C. Becknell [US], Reddeppa Reddy Dandu [US], Bruce D. Dorsey [US], Dimitar B. Gotchev [US], Robert L. Hudkins [US], Linda Weinberg [US], Craig A. Zificsak [US].
Full text: Click here
Patent 2024
1H NMR Dioxanes ethyl acetate Lincomycin methyl iodide n-hexane Oil, Mineral Silica Gel sodium hydride Sulfoxide, Dimethyl
5
Synthesis of Pyridine-Containing Compounds
Not available on PMC !

Example 21

[Figure (not displayed)]
[Figure (not displayed)]

Synthesis of 153-A.

To a mixture of 4-chloropyridin-3-amine (30.0 g, 234.4 mmol) and TEA (47.3 g, 468.8 mmol) in THF (600 mL) was added methyl 2-chloro-2-oxoacetate (30.0 g, 246.2 mmol) dropwise at ice bath. The solution was stirred at room temperature for 2 h. The reaction mixture was diluted with water (100 mL) and then extracted with EtOAc (100 mL×3). The combined organics washed with brine (100 mL×3), dried over anhydrous Na2SO4 and then concentrated in vacuo. The residue was purified by column chromatography on silica gel (PE:EtOAc=10:1˜5:1) to give 153-A (31.0 g, 62%) as a white solid.

Synthesis of 153-B.

A mixture of 153-A (15.0 g, 70.1 mmol) and Lawesson's reagent (19.8 g, 49.1 mmol) in toluene (300 mL) was heated to reflux overnight. The reaction mixture was diluted with water (100 mL) and then extracted with EtOAc (100 mL×3). The combined organics washed with brine (100 mL×3), dried over anhydrous Na2SO4 and then concentrated in vacuo. The residue was purified by column chromatography on silica gel (PE:EtOAc=10:1˜3:1) to give 153-B (2.0 g, 15%) as a yellow solid.

Synthesis of 153-C.

A mixture of 153-B (2.0 g, 10.3 mmol) and PtO2 (400 mg) in acetic acid (100 mL) was stirred at 70° C. overnight under H2 atmosphere at 5 MPa. PtO2 was then removed by filtration through the Celite. The filtrate was concentrated and the residue was purified by column chromatography on silica gel (DCM:MeOH=50:1˜20:1) to give 153-C (820 mg, 40%) as a white solid.

Synthesis of 153-D.

A mixture of 153-C (360 mg, 1.82 mmol) and formaldehyde solution (37% w/w, 0.7 mL) and acetic acid (2 drops) in MeOH (10 mL) was stirred at 40° C. for 1 h, then NaBH(OAc)3, (772 mg, 3.64 mmol) was added into above solution. The reaction mixture was stirred at 40° C. for 2 h. The solution was cooled to room temperature. The solution was diluted with water (10 mL), extracted with EtOAc (10 mL×3). The combined organic layer was 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=50:1˜20:1) to give 153-D (350 mg, 91%) as a white solid.

Synthesis of 153-E.

A mixture of 153-D (350 mg, 1.65 mmol) and LiOH·H2O (139 mg, 3.30 mmol) in MeOH/H2O (10 mL/4 mL) was stirred at room temperature overnight. After the reaction was completed according to LCMS, MeOH was removed in vacuo. The aqueous was adjusted to pH=6 with 1N HCl. Then the solution was concentrated to dryness to give 196-D as a white solid, which was used directly to next step without further purification.

Synthesis of 154-F.

To a solution of CDI (161 mg, 0.99 mmol) in DMF (5 mL) was added 154-E (0.83 mmol, crude product from last step) in portions and the solution was stirred at room temperature for 1 h to give solution A. At the same time, to a solution of 143-B (193 mg, 0.83 mmol) in DMF (5 mL) was added NaH (60% in mineral oil) (66 mg, 1.65 mmol) in portions and the mixture was stirred at room temperature for 1 h to give solution B. Then, the solution A was added into the solution B dropwise and the resulting mixture continue to stir at room temperature for 1 h. After the reaction was completed according to LCMS, the mixture was poured into water (10 mL). The precipitate was collected by filtered and concentrated to dryness to give 154-F (150 mg, 44%) as a yellow solid.

Synthesis of 153.

A mixture of 169-C (150 mg, 0.36 mmol) and Pd/C (150 mg) in EtOAc (5 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=8:1) to give 153 (100 mg, 70%) as a white solid.

Compound 165 was synthesized in a similar manner using the appropriately substituted halogen variant of 153.

Compound 165.

80 mg, 57%, a yellow solid.

Compound 163 was synthesized in a similar manner using furan-2-ylboronic acid and the appropriately substituted halogen variant of 153.

Compound 163.

35 mg, 38%, a white solid.

Compound 164 was synthesized in a similar manner using pyridin-3-ylboronic acid and the appropriately substituted halogen variant of 153.

Compound 164.

10 mg, 14%, a yellow 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].
Full text: Click here
Patent 2024
Acetic Acid Acids Amines Anabolism Atmosphere Bath brine Celite Chromatography compound 21 Filtration Formalin furan Halogens Lawesson's reagent Lincomycin Oil, Mineral platinum oxide Silica Gel Toluene

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1
Mineral oil by Merck Group
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2
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M16 medium by Merck Group
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6
M2 medium by Merck Group
Sourced in United States, Germany, United Kingdom, France, Japan
M2 medium is a cell culture media formulation designed for the maintenance and cultivation of mouse embryos. It provides the necessary nutrients and growth factors to support the development and growth of mouse embryos in an in vitro environment.
7
Tcm 199 by Thermo Fisher Scientific
Sourced in United States, Spain, Canada, Denmark, Belgium, Japan
TCM-199 is a cell culture medium developed for the in vitro cultivation of various cell types, including mammalian cells. It provides the necessary nutrients and growth factors to support cell growth and maintenance. The formulation is designed to maintain the physiological pH and osmolality required for optimal cell performance.
8
M8410 by Merck Group
Sourced in Germany, United States, Japan, China
The M8410 is a laboratory equipment product offered by Merck Group. It is a high-precision analytical instrument designed for various applications in scientific research and testing. The core function of the M8410 is to provide accurate and reliable measurements, but a detailed description of its intended use or capabilities is not available.
9
Fetal bovine serum (fbs) by Thermo Fisher Scientific
Sourced in United States, China, United Kingdom, Germany, Australia, Japan, Canada, Italy, France, Switzerland, New Zealand, Brazil, Belgium, India, Spain, Israel, Austria, Poland, Ireland, Sweden, Macao, Netherlands, Denmark, Cameroon, Singapore, Portugal, Argentina, Holy See (Vatican City State), Morocco, Uruguay, Mexico, Thailand, Sao Tome and Principe, Hungary, Panama, Hong Kong, Norway, United Arab Emirates, Czechia, Russian Federation, Chile, Moldova, Republic of, Gabon, Palestine, State of, Saudi Arabia, Senegal
Fetal Bovine Serum (FBS) is a cell culture supplement derived from the blood of bovine fetuses. FBS provides a source of proteins, growth factors, and other components that support the growth and maintenance of various cell types in in vitro cell culture applications.
10
Light mineral oil by Merck Group
Sourced in United States, Germany
Light mineral oil is a clear, colorless, and highly refined liquid obtained from petroleum. It is commonly used as a lubricant and in various industrial and laboratory applications due to its low viscosity and inert properties.

More about "Oil, Mineral"

Petroleum, natural gas, coal, metallic ores, and industrial minerals are critical components of modern society.
These natural resources power industries, fuel transportation, and provide raw materials for a wide range of products.
Researchers in the field of oil and mineral resources investigate the geological formation, extraction, and utilization of these assets, exploring techniques for efficient and sustainable management.
The PubCompare.ai platform leverages advanced AI to streamline this research, helping scientists easily identify the most effective protocols and products to accelerate their work.
The platform allows users to quickly locate the best protocols from literature, pre-prints, and patents using advanced AI comparisons, maximizing research efficiency and identifying the most effective products for their needs.
Mineral oils, such as those derived from petroleum, are widely used in various applications, including as lubricants, solvents, and components in personal care products.
Span 80, a non-ionic surfactant, is often used in conjunction with mineral oils to enhance their performance.
Bovine serum albumin (BSA) and hyaluronidase are also commonly used in research and industrial applications involving oil and mineral resources.
In the field of cell culture media, M16 medium, M2 medium, and TCM-199 are examples of specialized formulations that may be utilized in research related to oil and mineral resources.
Additionally, M8410 and fetal bovine serum (FBS) are often employed as supplements or components in these media.
By leveraging the insights and capabilities of the PubCompare.ai platform, researchers can streamline their investigations, optimize protocols, and identify the most effective products to address the world's growing energy and resource needs, ultimately contributing to the sustainable management of oil and mineral assets.