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Piperazine

Q: Are there different types or variations of Piperazine?

Yes, there are several variations and derivatives of Piperazine. Some common examples include mono-substituted piperazines, di-substituted piperazines, and heterocyclic piperazine compounds. These different types can have unique pharmacological profiles and applications, depending on the specific substituents or ring structures.

Piperazine is a chemical compound with the formula C4H10N2.
It is a cyclic diamine that serves as a versatile building block in organic synthesis and pharmaceutical development.
Piperazine and its derivatives have a wide range of biological activities, including use as anthelmintic drugs, antidepressants, and antihistamines.
Reserach on piperazine is vital for developing new therapeutic agents and optimizing existing treatments.
PubCompare.ai can help researchers streamline their piperazine studies by identifying the most reproducible and accurate experimental protocols from the litureature, preprints, and patents using advanced AI-powered comparisons.

Most cited protocols related to «Piperazine»

Cultivation of Promastigote Leishmania and Trypanosoma

Cited 13 times

Promastigote form L. mexicana (WHO strain MNYC/BZ/62/M379), L. major Friedlin and their genetically modified derivatives were grown at 28°C in M199 medium (Life Technologies) supplemented with 2.2 g l⁻¹ NaHCO₃, 0.005% haemin, 40 mM 4-(2-Hydroxyethyl)piperazine-1-ethanesulfonic acid pH 7.4 and 10% FCS. Relevant selection drugs (Melford Laboratories Ltd.) were added to the medium at the following concentrations: 32 µg ml⁻¹ Hygromycin B, 20 µg ml⁻¹ Puromycin Dihydrochloride, 5 µg ml⁻¹ Blasticidin S Hydrochloride, 40 µg ml⁻¹ G-418 Disulfate, 50 µg ml⁻¹ Nourseothricin Sulfate and 25 µg ml⁻¹ Phleomycin. Trypanosoma brucei SmOx B4 [49 (link)] was grown in HMI-9 [54 (link)] at 37°C in 5% CO₂, T. brucei SmOx P9 in SDM-79 [55 (link)] at 28°C. Relevant selection drugs (Melford Laboratories Ltd.) were added to the medium at the following concentrations: 0.2 µg ml⁻¹ Puromycin Dihydrochloride, 5 µg ml⁻¹ Blasticidin S Hydrochloride, 5 µg ml⁻¹ G-418 Disulfate, 5 µg/ml Hygromycin B. Cell culture densities were measured using a CASY model TT cell counter (Roche Diagnostics) with a 60 µm capillary and exclusion of particles with a pseudo diameter below 2.0 µm.

Beneke T., Madden R., Makin L., Valli J., Sunter J, & Gluenz E. (2017). A CRISPR Cas9 high-throughput genome editing toolkit for kinetoplastids. Royal Society Open Science, 4(5), 170095.

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Publication 2017

antibiotic G 418 Bicarbonate, Sodium blasticidin S Capillaries Cells derivatives Diagnosis ethane sulfonate Hemin Hygromycin B L Forms Nourseothricin Pharmaceutical Preparations Phleomycins Piperazine Puromycin Dihydrochloride Strains Sulfates, Inorganic Trypanosoma brucei brucei

Optimized Synthesis of Isotopically Labeled M2TM

Cited 13 times

Due to the requirements for a large quantity of isotopically labeled peptides and the hydrophobic nature of M2TM, we developed an optimized procedure that delivers crude peptide with >80% purity. Problems encountered in obtaining high-yields and purity included aspartamide formation at residue 44 and slow coupling near the center of the chain. M2TM(22–46) with uniformly ¹³C, ¹⁵N-labeled V27, A30 and G34 (VAG-M2TM) was synthesized using Fmoc chemistry at elevated temperature (75°C for both coupling and deprotection) in a semiautomated Quest synthesizer using Rink Amide Chemmatrix resin (Matrix Innovation Inc, Canada). Coupling reagent were 5 eq amino acid, 5 eq HCTU, 10 eq DIEA in NMP for 5 mins coupling. 5% piperazine and 0.1 M HOBt in DMF were used as the deprotection solution in order to minimize aspartamide formation. The peptide was cleaved from the resin using 95% TFA, 2.5% Tris, 2.5% H₂O and precipitated from ether after removal of TFA. Ether was decanted after centrifugation and the peptide was washed with cold ether again. The final peptide was dissolved in 50% B′ (59.9% isopropanol, 30% acetonitrile, 10% H₂O, and 0.1% TFA) and 50% A (99.9% H₂O, 0.1% TFA) and purified by preparative C4 reverse phase HPLC with a linear gradient of 70% B′ to 85% B′. The peptide was eluted at 78% B′. The purity and identify of the peptide was confirmed by analytical HPLC (>98% purity) and MALDI-MS. Calculated MS: 2782.38, Observed MS: 2782.90.

Cady S.D., Wang J., Wu Y., DeGrado W.F, & Hong M. (2011). Specific Binding of Adamantane Drugs and Direction of their Polar Amines in the Pore of the Influenza M2 Transmembrane Domain in Lipid Bilayers and Dodecylphosphocholine Micelles Determined by NMR Spectroscopy. Journal of the American Chemical Society, 133(12), 4274-4284.

Publication 2011

1-hydroxybenzotriazole acetonitrile Amino Acids Centrifugation Cold Temperature Ethers Fever High-Performance Liquid Chromatographies Isopropyl Alcohol N,N-diisopropylethylamine Peptides Piperazine Resins, Plant Rink amide resin Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization Tromethamine

Folate Extraction and Quantification from Cells

Cited 10 times

Folates were extracted from cultured cells in 6 cm plates by aspirating media and immediately adding 1 mL ice cold 50:50 H₂O:MeOH containing 25 mM sodium ascorbate and 25 mM NH₄OAc at pH 7. Plates were kept on ice and cells were scraped and the resulting mixture of cells and solvent transferred to 1.5 mL centrifuge tubes after 30 min. Tubes were heated to 60 °C for 5 min to fully denature proteins, and precipitates were removed by centrifugation at 16000 × g for 5 min at 4 °C. To cleave glutamate tails, supernatants were dried under N₂ flow and resuspended in 450 μL potassium phosphate buffer (50 mM with 30 mM ascorbic acid and 0.5% 2-mercaptoethanol at pH 7). 25 μL rat serum pretreated with activated charcoal to remove endogenous folate (3 (link)) was added to the samples before incubating at 37 °C for 2 h. We measured folate content in the serum before and after activated charcoal treatment, and the charcoal-treatment depleted rat serum folates to undetectable levels. To clean up samples before LC-MS, Bond Elut-PH SPE columns (Agilent) were conditioned with 1 mL MeOH and then with 1 mL wash buffer (30 mM ascorbic acid in 25 mM NH₄OAc buffer at pH 4.0). After adjusting the samples to pH 4 with 7 μL of 40% formic acid solution at 4°C, the samples were loaded onto the conditioned SPE columns, washed with 1 mL wash buffer and subsequently eluted with 400 μL elution buffer (50:50 H₂O:MeOH containing 0.5% 2-mercaptoethanol and 25 mM NH₄OAc at pH 7). The eluate was dried down under N₂ flow, resuspended into HPLC water, centrifuged to remove possible precipitate, kept at 4°C in an autosampler and analyzed by LC-MS within 12 h to minimize degradation. Sample analysis was the same as described above with modification in the LC gradient, 0 min, 0% B; 2.5 min, 0% B; 5 min, 50% B; 13 min, 95% B; 14 min, 0% B; 20 min, 0% B. Mass spectrometry setup was the same except the scan window was m/z = 400 to 1000. In the case of NaBH₃CN or NaBD₃CN reduction, before cell extraction, 1 M NaBH₃CN or NaBD₃CN stock solution was added to 50:50 H₂O:acetonitrile extraction buffer containing 25 mM sodium ascorbate and 25 mM HEPES (4-(2-hydroxyethyl)piperazine-1-ethanesulfonic acid) at pH 7 to a final concentration of 25 mM. Acetonitrile was used in place of methanol for extraction prior to derivatization, to avoid potential impact of formaldehyde, which is an impurity in methanol. The subsequent procedure was identical except 4 μL of 40% formic acid was added to adjust pH to 4 before SPE purification. For quantification of total pool size of THF species, 4 pmol of different THF species standards were spiked in to cell extracts before heat treatment.

Chen L., Ducker G.S., Lu W., Teng X, & Rabinowitz J.D. (2017). An LC-MS Chemical Derivatization Method for the Measurement of Five Different One-carbon States of Cellular Tetrahydrofolate. Analytical and bioanalytical chemistry, 409(25), 5955-5964.

Publication 2017

2-Mercaptoethanol acetonitrile Ascorbic Acid Buffers Cells Centrifugation Charcoal Charcoal, Activated Cold Temperature Cultured Cells ethane sulfonate Folate Formaldehyde formic acid Glutamate HEPES High-Performance Liquid Chromatographies Mass Spectrometry Methanol Piperazine potassium phosphate Proteins Radionuclide Imaging Serum Sodium Ascorbate Solvents Tail

Cyanobacterial Metabolite Extraction Protocol

Cited 9 times

Cell sampling was performed according to a previously reported method (Huege et al., 2011 (link)), with minor modifications. Cyanobacterial cells, equivalent to 5 or 10mg dry weight, were removed from cultivation vessels and filtered using 10 μm (for A. platensis) or 1 μm (for Synechocystis sp. PCC6803) pore size Omnipore filter disks (Millipore, MA, USA). After washing with 260mM (for A. platensis) or 20mM (for Synechocystis sp. PCC6803) ammonium bicarbonate pre-chilled to 4 ºC, cells retained on the filters were immediately placed into 2ml of pre-cooled (–30 ºC) methanol containing 190nM (+)-10-camphorsulfonic acid, 31 μM L-methionine sulfone, and 31 μM piperazine-1,4-bis(2-ethanesulfonic acid) (PIPES) as internal standards for mass analysis. Intracellular metabolites were extracted using a cold 10:3:1 (v/v/v) methanol:chloroform:water solution, as described previously (Bölling and Fiehn, 2005 (link)). Cells were suspended by vortexing and then 1ml of the cell suspension was mixed with 100 μl of pre-cooled (4 ºC) water and 300 μl of chloroform containing 15 μM trans-β-apo-8′-carotenal as an internal standard for pigment analysis. The cell suspension was shaken at 1200rpm (MBR-022UP; TAITEC, Saitama, Japan) for 30min at 4 ºC in the dark before centrifugation at 14 000g for 5min at 4 ºC. Next, 980 μl of cell extract obtained as the supernatant was transferred to a clean tube. After adding 440 μl of water, phase separation of aqueous and organic layers was performed by centrifugation at 14 000g for 5min at 4 ºC. Two aliquots (450 μl each) of the aqueous layer were transferred to clean tubes for analysis by capillary electrophoresis/mass spectrometry (CE/MS) and liquid chromatography/triple quadrupole mass spectrometry (LC/QqQ-MS). After filtration with a Millipore 5kDa cut-off filter for the removal of solubilized proteins, the aqueous-layer extracts were evaporated under vacuum using a FreeZone 2.5 Plus freeze dry system (Labconco, Kansas City, MO, USA). Dried extracts were stored at –80 °C until used for mass analysis. A 50 μl aliquot of the organic layer obtained by phase separation was stored at –80 °C for subsequent pigment analysis.

Hasunuma T., Kikuyama F., Matsuda M., Aikawa S., Izumi Y, & Kondo A. (2013). Dynamic metabolic profiling of cyanobacterial glycogen biosynthesis under conditions of nitrate depletion. Journal of Experimental Botany, 64(10), 2943-2954.

Publication 2013

10-camphorsulfonic acid ammonium bicarbonate Blood Vessel Cell Extracts Cells Centrifugation Chloroform Cold Temperature Cyanobacteria Electrophoresis, Capillary ethane sulfonate Filtration Freezing Liquid Chromatography Mass Spectrometry Methanol methionine sulfone Pigmentation Piperazine piperazine-N,N'-bis(2-ethanesulfonic acid) Proteins Protoplasm Spectrometry Strains Synechocystis Vacuum

Synthesis and Validation of LDN-193189

Cited 9 times

We purchased dorsomorphin (Compound C, 6-[4-(2-piperidin-1-yl-ethoxy)phenyl]-3-pyridin-4-yl-pyrazolo[1,5-a]pyrimidine) from EMD Biosciences. We synthesized LDN-193189 (4-[6-(4-piperazin-1-ylphenyl)pyrazolo[1,5-a]pyrimidin-3-yl]quinoline) as previously described6 (link), determined its purity (99.8%) by HPLC and confirmed its structure by ¹H-NMR and high-resolution mass spectrometry. The vehicle was 2% (wt/vol) (2-hydroxypropyl)-β-cyclodextrin in PBS, pH 7.4. We purchased dexamethasone from Sigma. Recombinant human BMP4, platelet-derived growth factor-BB and TGF-β were obtained from R&D Systems. We produced adenoviruses expressing GFP and Cre and quantified them by the plaque-titer method.

Yu P.B., Deng D.Y., Lai C.S., Hong C.C., Cuny G.D., Bouxsein M.L., Hong D.W., McManus P.M., Katagiri T., Sachidanandan C., Kamiya N., Fukuda T., Mishina Y., Peterson R.T, & Bloch K.D. (2008). BMP type I receptor inhibition reduces heterotopic ossification. Nature medicine, 14(12), 1363-1369.

Publication 2008

1H NMR Adenoviruses Becaplermin Bone Morphogenetic Protein 4 Cyclodextrins Dental Plaque Dexamethasone dorsomorphin High-Performance Liquid Chromatographies Homo sapiens Hypromellose LDN 193189 Mass Spectrometry Piperazine Pyrimidines quinoline Transforming Growth Factor beta

Most recents protocols related to «Piperazine»

Synthesis of 2,5-Difluoro-4-Aminophenyl Piperazine Derivative

Not available on PMC !

Example 161

[Figure (not displayed)]

To a solution of 2-(piperazin-1-yl)ethanol (0.73 g, 5.6 mmol, 1 eq.) in DMF (10 mL) was added K₂CO₃(1.56 g, 11.3 mmol, 2 eq.) followed by 1,2,4-trifluoro-5-nitrobenzene (1 g, 5.6 mmol, 1 eq.) and the mixture was stirred at 0° C. for 1 hour. The mixture was poured into ice-water (100 mL), extracted by EA (3×40 mL), and the organic layers were combined, washed with brine (150 mL), concentrated and purified via column chromatography (10-95% CH₃CN—H₂O) to afford 2-(4-(2,5-difluoro-4-nitrophenyl)piperazin-1-yl)ethanol (0.65 g, 41%) as a yellow solid.

[Figure (not displayed)]

To a solution of 2-(4-(2,5-difluoro-4-nitrophenyl)piperazin-1-yl)ethanol (0.65 g, 2.3 mmol) in MeOH (50 mL) was added Pd/C (100 mg) and the resulting mixture was stirred at r.t. overnight. The Pd/C was removed by filtration and the filtrate was concentrated to afford 2-(4-(4-amino-2,5-difluorophenyl)piperazin-1-yl)ethanol (0.58 g, 99%).

[Figure (not displayed)]

To a suspension of 2-(4-(4-amino-2,5-difluorophenyl)piperazin-1-yl)ethanol (270 mg, 0.88 mmol, 1 eq.) and N-(3-(2-chloroquinazolin-8-yl)phenyl)acrylamide (225 mg, 0.88 mmol, 1 eq.) in n-BuOH (10 mL) was added TFA (0.5 mL, 4.4 mmol, 5 eq.) and the resulting mixture was stirred at 90° C. overnight. The mixture was concentrated, diluted with DCM (20 mL), washed with Na₂CO₃solution (20 mL), dried, concentrated and purified via column chromatography (DCM/MeOH=10/1) to afford N-(3-(2-((2,5-difluoro-4-(4-(2-hydroxyethyl)piperazin-1-yl)phenyl)amino)quinazolin-8-yl)phenyl)acrylamide (120 mg, 26%) as yellow solid. LRMS (M+H⁺) m/z calculated 531.2, found 531.2. 1H NMR (DMSO-d6, 400 MHz) δ 10.18 (s, 1H), 9.37 (s, 1H), 9.17 (s, 1H), 7.97-7.94 (m, 3H), 7.83-7.74 (m, 2H), 7.50-7.39 (m, 3H), 6.90-6.85 (m, 1H), 6.48-6.41 (m, 1H), 6.23 (dd, 1H), 5.73 (dd, 1H), 4.42 (t, 1H), 3.55-3.50 (m, 2H), 2.94-2.91 (m, 4H), 2.55-2.54 (m, 4H), 2.44 (t, 2H).

US11865120B2. Substituted quinazolines for inhibiting kinase activity (2024-01-09). NeuPharma, Inc [US]. Inventors: Xiangping Qian [US], Yong-Liang Zhu [US].

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Patent 2024

1H NMR Acrylamide brine Chromatography Ethanol Filtration Ice Nitrobenzenes Piperazine potassium carbonate Sulfoxide, Dimethyl

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 NaHCO₃and extracted with DCM. The organic layer was dried over Na₂SO₄and 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].

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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

Synthesis and Characterization of Pyrrolo-pyridine Derivatives

Not available on PMC !

Example 264

[Figure (not displayed)]

A mixture of (2R,5S)-4-{2-[6-(2,4-difluoro-benzyl)-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridin-1-yl]-2-oxo-ethyl}-2-methyl-5-((R)-3-methyl-morpholin-4-ylmethyl)-piperazine-1-carboxylic acid tert-butyl ester (0.103 g), ethyl acetate (10 mL) and 4 M HCl in dioxan (10 mL) was stirred at 20° C. for 18 h and the resulting solid collected by filtration to give the title compound (0.075 g). ¹H NMR (Me-d3-OD): 8.76 (1H, s), 8.48 (1H, s), 7.56-7.44 (1H, m), 7.11-6.98 (2H, m), 4.27 (5H, d), 4.16-3.96 (5H, m), 3.82 (3H, s), 3.66-3.41 (5H, m), 3.18 (4H, d), 1.62 (6H, s), 1.41 (6H, br m). MS: [M+H]⁺=528.

Example 265

[Figure (not displayed)]

Prepared from (R)-4-{2-[6-(4-Fluoro-benzyl)-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridin-1-yl]-2-oxo-ethyl}-2-methyl-piperazine-1-carboxylic acid tert-butyl ester in an analogous manner to Example 264. ¹H NMR (Me-d3-OD): 8.75 (1H, s), 8.37 (1H, s), 7.33 (2H, dd), 7.09 (2H, t), 4.41 (2H, s), 4.19 (2H, s), 4.16 (2H, s), 3.87-3.68 (4H, m), 3.61-3.41 (2H, m), 3.27 (1H, t), 1.59 (6H, s), 1.44 (3H, d). MS: [M+H]⁺=397.

US11866428B2. Bicyclic heterocycle compounds and their uses in therapy (2024-01-09). ASTEX THERAPEUTICS LIMITED [GB]. Inventors: Alison Jo-Anne Woolford [GB], Steven Howard [GB], Ildiko Maria Buck [GB], Gianni Chessari [GB], Christopher Norbert Johnson [GB], Emiliano Tamanini [GB], James Edward Harvey Day [GB], Elisabetta Chiarparin [GB], Thomas Daniel Heightman [GB], Martyn Frederickson [GB], Charlotte Mary Griffiths-Jones [GB].

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Patent 2024

1H NMR 2-methyl piperazine Bridged Bicyclo Compounds, Heterocyclic Carboxylic Acids dioxane Esters ethyl acetate Filtration Piperazine TERT protein, human Therapeutics

Synthesis of N-(3-(2-((4-(4-(2,2-difluoroethyl)piperazin-1-yl)phenyl)amino)quinazolin-8-yl)phenyl)acrylamide

Not available on PMC !

Example 58

[Figure (not displayed)]

N-(3-(2-((4-(4-(2,2-difluoroethyl)piperazin-1-yl)phenyl)amino)quinazolin-8-yl)phenyl)acrylamide (74.2 mg) was prepared as described for (S)—N-(3-(2-((4-((1-acetylpyrrolidin-3-yl)oxy)phenyl)amino)quinazolin-8-yl)phenyl)acrylamide. LRMS (M+H⁺) m/z calculated 515.2, found 515.2. ¹H NMR (CD₃OD, 300 MHz) δ 9.15 (s, 1H), 7.52-7.99 (m, 6H), 7.39-7.50 (m, 3H), 6.80 (d, 2H), 6.41-6.52 (m, 2H), 6.02 (t, 1H), 5.77-5.84 (m, 1H), 3.03-3.12 (m, 4H), 2.74-2.88 (m, 6H).

US11865120B2. Substituted quinazolines for inhibiting kinase activity (2024-01-09). NeuPharma, Inc [US]. Inventors: Xiangping Qian [US], Yong-Liang Zhu [US].

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Patent 2024

1H NMR Acrylamide Piperazine

Synthesis of Novel Quinazoline Derivative

Not available on PMC !

Example 35

[Figure (not displayed)]

8-(2-Fluoro-5-(2-morpholinoethoxy)phenyl)-N-(4-(piperazin-1-yl)phenyl)quinazolin-2-amine (53.4 mg) was prepared as described for N-(4-morpholinophenyl)-8-phenylquinazolin-2-amine. LRMS (M+H⁺) m/z calculated 529.3, found 529.3. ¹H NMR (CDCl₃, 400 MHz) δ 9.08 (s, 1H), 7.78 (t 2H), 7.57 (d, 2H), 7.39 (t, 1H), 7.25 (s, 1H), 7.16 (t, 1H), 7.06-7.14 (m, 3H), 6.79 (d, 2H), 4.091 (t, 2H), 3.69 (t, 4H), 3.20 (m, 8H), 2.78 (t, 2H), 2.54 (m, 4H).

US11865120B2. Substituted quinazolines for inhibiting kinase activity (2024-01-09). NeuPharma, Inc [US]. Inventors: Xiangping Qian [US], Yong-Liang Zhu [US].

Full text: Click here

Patent 2024

1H NMR Amines Piperazine

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Piperazine is a heterocyclic organic compound with the chemical formula C4H10N2. It is a colorless crystalline solid with a melting point of 108-113°C. Piperazine is used as a building block in the synthesis of various pharmaceutical and chemical products.

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Penicillin/streptomycin is a commonly used antibiotic solution for cell culture applications. It contains a combination of penicillin and streptomycin, which are broad-spectrum antibiotics that inhibit the growth of both Gram-positive and Gram-negative bacteria.

What are the common uses of Piperazine?

Piperazine has a wide range of biological activities and is used in various applications. It is commonly employed as an anthelmintic drug to treat parasitic worm infections, as an antidepressant, and as an antihistamine. Piperazine and its derivatives are also useful building blocks in organic synthesis and pharmaceutical development for creating new therapeutic agents.

Are there different types or variations of Piperazine?

What are some common challanges in working with Piperazine?

One of the main challenges in working with Piperazine is ensuring reproducibility and accuracy of experimental protocols. Piperazine research often involves testing different derivatives, formulations, and application methods, which can lead to variability in results. This is where a tool like PubCompare.ai can be extremely useful in identifying the most reliable and effective protocols from the literature, preprints, and patents.

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More about "Piperazine"

Piperazine is a versatile chemical compound with the formula C4H10N2, belonging to the class of cyclic diamines.
This versatile building block has a wide range of biological activities, making it a crucial component in organic synthesis and pharmaceutical development.
Piperazine and its derivatives have found applications as anthelmintic drugs, antidepressants, and antihistamines, highlighting the importance of research in this area for developing new therapeutic agents and optimizing existing treatments.
When conducting piperazine research, it is essential to consider the use of various related compounds and additives, such as Fetal Bovine Serum (FBS), Bovine Serum Albumin (BSA), Dimethyl Sulfoxide (DMSO), and 4-(2-Hydroxyethyl)piperazine-1-ethanesulfonic Acid (HEPES).
These substances can play crucial roles in cell culture, buffer preparation, and other experimental protocols.
Additionally, common laboratory reagents like HEPES, Sodium Chloride (NaCl), Penicillin, and Streptomycin may be utilized in piperazine-related studies.
To streamline your piperazine research, PubCompare.ai, the leading AI-driven platform, can be a valuable tool.
This innovative solution helps researchers identify the most reproducible and accurate experimental protocols from the literature, preprints, and patents, using advanced AI-powered comparisons.
By leveraging PubCompare.ai, you can optimize your piperazine experiments and stay at the forefront of this important field of study.