Hydrazine hydrate (1:1) → HCID 178508269, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-{2-amino-6-[2-(5-chloro-1H-benzimidazol-2-yl)-4-morpholinyl]-4-pyrimidinyl}-2-fluorobenzonitrile (140 mg, 0.311 mmol) in ethanol (5 mL) stirred at room temperature was added hydrazine hydrate (156 mg, 3.11 mmol), and the reaction mixture was stirred overnight at 85° C. The solvent was evaporated in vacuo to give the crude product. The crude product was added to a silica gel column and was eluted with CH2Cl2/MeOH to afford the title compound (41 mg) as a yellow solid. LC-MS (ES) m/z=462 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 3.13-3.17 (m, 2H), 3.81 (t, J=13.2 Hz, 1H), 4.12 (d, J=9.6 Hz, 1H), 4.35 (d, J=9.6 Hz, 1H), 4.84-4.89 (m, 2H), 5.40 (s, 2H), 6.30 (s, 2H), 6.72 (s, 1H), 7.22 (t, J=9.6 Hz, 1H), 7.48-7.50 (m, 1H), 7.60-7.73 (m, 3H), 7.97 (s, 1H), 11.55 (s, 1H), 12.80 (m, 1H).

Provenance & Evidence