Hydrazine → HCID 178508271, compound
Reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10](F)[CH:9]=2)[CH:5]=[C:4]([N:17]2[CH2:22][CH2:21][O:20][CH:19]([C:23]3[NH:24][C:25]4[CH:30]=[CH:29][N:28]=[CH:27][C:26]=4[N:31]=3)[CH2:18]2)[N:3]=1.[NH2:32][NH2:33]>C(O)C>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[C:10]3[C:11]([C:12]([NH2:13])=[N:32][NH:33]3)=[CH:14][CH:15]=2)[CH:5]=[C:4]([N:17]2[CH2:22][CH2:21][O:20][CH:19]([C:23]3[NH:24][C:25]4=[CH:30][CH:29]=[N:28][CH:27]=[C:26]4[N:31]=3)[CH2:18]2)[N:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 4-{2-amino-6-[2-(1H-imidazo[4,5-c]pyridin-2-yl)-4-morpholinyl]-4-pyrimidinyl}-2-fluorobenzonitrile (380 mg, 0.913 mmol) and hydrazine (1.432 mL, 45.6 mmol) in ethanol (3 mL) was heated under microwave conditions with stirring for 1 hour. The mixture was concentrated. Water (20 mL) was added, and the resulting mixture was filtered to afford the crude title compound (135 mg) as a brown solid. This material was combined with another sample of the title compound (25 mg), and the combined material was purified by preparative HPLC using CH3CN in water (10 mmol ammonium hydrogen carbonate in water) from 40% to 60% in 9 min to afford the title compound (21 mg) as an off-white solid. LC-MS (ES) m/z=429 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 3.13-3.22 (m, 2H), 3.81-3.91 (m, 1H), 4.14 (d, J=11.2 Hz, 1H), 4.34 (d, J=11.6 Hz, 1H), 4.91 (dd, J=10.0 Hz, 2H), 5.39 (s, 2H), 6.25 (s, 2H), 6.72 (s, 1H), 7.54 (s, 1H), 7.62 (m, 1H), 7.72 (d, J=8.8 Hz, 1H), 7.97 (s, 1H), 8.31 (d, J=5.6 Hz, 1H), 8.91 (s, 1H), 11.54 (s, 1H), 13.01 (s, 1H).