N-(2-nitro-5-(pyrazin-2-yl)phenyl)pyrrolidine-1-carboxamide → N-(2-amino-5-(pyrazin-2-yl)phenyl)pyrrolidine-1-carboxamide

反応式

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[N:14][CH:13]=[CH:12][N:11]=2)=[CH:6][C:5]=1[NH:16][C:17]([N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)=[O:18])([O-])=O>CO.C1COCC1.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[N:14][CH:13]=[CH:12][N:11]=2)=[CH:6][C:5]=1[NH:16][C:17]([N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)=[O:18]

参加物

実験手順

To a solution of 1 N-(2-nitro-5-(pyrazin-2-yl)phenyl)pyrrolidine-1-carboxamide (0.11 g, 0.35 mmol) in methanol (6 mL) and THF (6 mL) was added Pd/C (0.04 g, 0.94 mmol, 0.33 equiv.). The reaction mixture was degassed then stirred at room temperature under H2 atmosphere for 1 h. The reaction was filtered through celite and concentrated. The crude solid was washed with ether, and dried under reduced pressure to obtain of pure N-(2-amino-5-(pyrazin-2-yl)phenyl)pyrrolidine-1-carboxamide (0.07 g, 70% yield). ESI+ MS: m/z 284([M+H]+), 1H NMR (500 MHz, d6-DMSO): δ 9.30 (s, 1H), 8.55 (s, 1H), 8.40-8.39 (m, 1H), 7.88 (s, 1H), 7.71-7.69 (m, 1H), 7.53 (s, 1H), 6.81 (d, J=8.5 Hz, 1H), 5.31 (s, 2H), 3.40-3.37 (m, 4H), 1.86 (m, 4H).