Hydrazine → HCID 178489840, compound

Participants

Reaction Steps

A mixture of 4-[2-amino-6-(2-{4-[3-(methyloxy)phenyl]-1H-imidazol-2-yl}-4-morpholinyl)-4-pyrimidinyl]-2-fluorobenzonitrile (700 mg, 1.485 mmol) and hydrazine (2.35 mL, 74.2 mmol) in ethanol (8.0 mL) was heated under microwave conditions with stirring for 1 hour. The mixture was concentrated, and water (20 mL) was added. The resulting mixture was filtered to afford the crude title compound (725 mg) as a yellow solid. This material was combined with another sample of the title compound (25 mg). The combined material was washed with CH2Cl2 (2×25 mL) and EtOAc (2×20 mL), and dried under high vacuum to afford the title compound (216 mg) as a yellow solid. LC-MS (ES) m/z=484 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 3.08-3.15 (m, 1H), 3.23 (d, J=8.8 Hz, 1H), 3.69-3.76 (m, 1H), 3.79 (s, 3H), 4.05 (d, J=11.2 Hz, 1H), 4.33 (d, J=9.6 Hz, 1H), 4.62 (dd, J=10.0 Hz, 2.4 Hz, 1H), 4.73 (s, 1H), 5.38 (s, 2H), 6.21 (s, 2H), 6.71 (s, 1H), 6.76 (d, J=8.2 Hz, 1H), 7.25 (t, J=8.0 Hz, 1H), 7.35-7.37 (m, 2H), 7.54-7.63 (m, 2H), 7.71 (d, J=8.4 Hz, 1H), 7.97 (s, 1H), 11.52 (s, 1H), 12.34 (s, 1H).

Provenance & Evidence