3047-38-9, name is Cyclopent-1-enecarbonitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. name: Cyclopent-1-enecarbonitrile
Into a 5000-mL 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed 4-(benzyloxy)-lH-pyrazolo[4,3-c]pyridin-3-amine (1-1; 250 g, 1.04 mol), ethanol (3000 mL), cyclopent-l-ene-l-carbonitrile (300 g, 3.22 mol), and DBU (317 g, 2.08 mol). The resulting solution was heated to reflux and stirred overnight. The reaction mixture was cooled and concentrated in vacuo, and the resulting residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1 : 10-1 :2) to afford racemic-2-[3- amino-4-(benzyloxy)- lH-pyrazolo[4,3-c]pyridin- 1 -yljcyclopentane- 1 -carbonitrile. The racemic 2-[3-amino-4-(benzyloxy)- lH-pyrazolo[4,3-c]pyridin- 1 – yljcyclopentane- 1 -carbonitrile (100 g, 300 mmol) was purified using Chiral Prep-SFC with the following conditions: Column Used: Phenomenex Lux Cellulose-4, 2 x 25cm, 5 muiotaeta Mobile phase: C02 (80%), methanol with 0.1% DEA (20%) Wavelength: UV 254 nm. Peak A, 1-6: (lR,2R)-2-[3-amino-4-(benzyloxy)-lH-pyrazolo[4,3-c]pyridin-l-yl]cyclopentane- 1 -carbonitrile LRMS(ESI) calc’d for C19H20N5O [M+H] +: 334, found 334. 1H-NMR(300MHz, CDCI3): delta 7.86-6.84 (m, 7H), 5.55 (s, 2H), 4.94-4.86 (s, 2H), 4.49 (s, 1H), 3.34-3.26 (m, 1H), 2.39-2.01 (m, 6H). Peak B, 1-7: (llS’,2lS,)-2-[3-amino-4-(benzyloxy)-lH-pyrazolo[4,3-c]pyridin-l-yl]cyclopentane-l- carbonitrile LRMS(ESI) calc’d for C19H20N5O [M+H] +: 334, found 334. 1H-NMR(300MHz, CDCI3): delta 7.86-6.84 (m, 7H), 5.55 (s, 2H), 4.94-4.86 (s, 2H), 4.49 (s, 1H), 3.34-3.26 (m, 1H), 2.39-2.01 (m, 6H).
The synthetic route of 3047-38-9 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; MERCK SHARP & DOHME CORP.; CHILDERS, Matthew Lloyd; DINSMORE, Christopher; FULLER, Peter; GUERIN, David; KATZ, Jason David; PU, Qinglin; SCOTT, Mark E.; THOMPSON, Christopher F.; ZHANG, Hongjun; FALCONE, Danielle; TORRES, Luis; BRUBAKER, Jason; ZENG, Hongbo; CAI, Jiaqiang; DU, Xiaoxing; WANG, Chonggang; BAI, Yunfeng; KONG, Norman; LIU, Yumei; ZHENG, Zhixiang; WO2014/146490; (2014); A1;,
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