Adding a certain compound to certain chemical reactions, such as: 37599-58-9, name is (1H-Pyrazol-3-yl)methanamine, belongs to pyrazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 37599-58-9, Recommanded Product: (1H-Pyrazol-3-yl)methanamine
To a solution of 4-chloro-7-(l-(tetrahydro-2H-pyran-2-yl)-lH-pyrazol-5- yl)quinolin-2-amine (20 mg, 0.061 mmol) and (lH-pyrazol-3-yl)methanamine (59.1 mg, 0.608 mmol) in DMSO (0.5 mL) was added Hunig’s Base (0.032 mL, 0.182 mmol). The reaction was heated to 120 C overnight. The reaction was cooled, diluted with water, and extracted three times with EtOAc. The organic layers were concentrated, then dissolved in 0.4 mL DCM and 0.4 mL TFA. After 1 hour, the reaction was complete by LCMS. The reaction was concentrated and azeotroped with DCM. The residue was dissolved in DMF, filtered through a syringe filter, and the crude material was purified via preparative LC/MS with the following conditions: Column: XBridge CI 8, 200 mm x 19 mm, 5-muiotatauiota particles; Mobile Phase A: 5:95 acetonitrile: water with 0.1%trifluoroacetic acid; Mobile Phase B: 95:5 acetonitrile: water with 0.1% trifluoroacetic acid; Gradient: a 0-minute hold at 0% B, 0-40% B over 20 minutes, then a 4-minute hold at 100% B; Flow Rate: 20 mL/min; Column Temperature: 25 C. Fraction collection was triggered by MS signals. Fractions containing the desired product were combined and dried via centrifugal evaporation. The material was further purified via preparative LC/MS with the following conditions: Column: XBridge C18, 200 mm x 19 mm, 5-mupiiota particles; Mobile Phase A: 5:95 acetonitrile: water with 10-mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile: water with 10-mM ammonium acetate; Gradient: a 3- minute hold at 0% B, 0-32% B over 25 minutes, then a 5-minute hold at 100% B; Flow Rate: 20 mL/min; Column Temperature: 25 C. Fraction collection was triggered by MS signals. Fractions containing the desired product were combined and dried via centrifugal evaporation to give N4-((lH-pyrazol-3-yl)methyl)-7-(lH-pyrazol-5-yl)quinoline-2,4- diamine (4.6 mg, 24.7%). NMR (500 MHz, DMSO-de) delta 8.00 (br d, J=8.2 Hz, 1H),7.75 (s, 1H), 7.72 (br s, 1H), 7.58 (br s, 1H), 7.54 (br d, J=7.9 Hz, 1H), 7.43 (br s, 1H),6.76 (s, 1H), 6.62 – 6.41 (m, 1H), 6.20 (s, 1H), 5.76 (s, 1H), 4.42 (br d, J=5.2 Hz, 2H). LC RT: 0.99 min. M/Z= 306.18. (1550)
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Reference:
Patent; INNATE TUMOR IMMUNITY, INC.; O’MALLEY, Daniel; GAVAI, Ashvinikumar V.; GILL, Patrice; TARBY, Christine M.; WATTERSON, Scott Hunter; GONG, Hua; WILLIAMS, David K.; GHOSH, Shomir; ROUSH, William R.; (307 pag.)WO2019/14402; (2019); A1;,
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