Hydrazine → 6-{2-Amino-6-[2-(4,5,6,7-tetrahydro-1H-benzimidazol-2-yl)-4-morpholinyl]-4-pyrimidinyl}-1H-indazol-3-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-{2-amino-6-[2-(4,5,6,7-tetrahydro-1H-benzimidazol-2-yl)-4-morpholinyl]-4-pyrimidinyl}-2-fluorobenzonitrile (150 mg, 0.358 mmol) and hydrazine (1.13 mL, 35.8 mmol) in ethanol (4 mL) was heated at 120° C. under microwave conditions with stirring for 1 hour. The solvent was evaporated to get 200 mg of residue, which was purified by preparative HPLC to afford the title compound (42 mg) as a yellow powder. LC-MS (ES) m/z=432 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.71 (s, 4H), 2.42 (s, 2H), 3.12-2.99 (m, 2H), 3.66 (dt, J=11.6 Hz, 2.4 Hz, 1H), 4.00 (dd, J=11.6 Hz, 2.0 Hz, 1H), 4.33-4.30 (m, 1H), 4.44 (dd, J=10.8 Hz, 2.4 Hz, 1H), 4.62 (bs, 1H), 5.28 (s, 2H), 6.18 (s, 2H), 6.66 (s, 1H), 7.61 (dd, J=8.4 Hz, 0.8 Hz, 1H), 7.71 (d, J=8.4 Hz, 1H), 7.97 (s, 1H), 11.51 (s, 1H), 11.68 (s, 1H).

Provenance & Evidence