Hydrazine hydrate (1:1) → HCID 178508270, compound

Participants

Reaction Steps

To a solution of 4-{2-amino-6-[2-(5-fluoro-1H-benzimidazol-2-yl)-4-morpholinyl]-4-pyrimidinyl}-2-fluorobenzonitrile (120 mg, 0.277 mmol) in ethanol (3.0 mL) at room temperature was added hydrazine hydrate (139 mg, 2.77 mmol). The reaction vessel was sealed and heated in Biotage Initiator using initial high to 120° C. for 1 hour. After cooling the reaction, the solvent was evaporated in vacuo to give the crude product which was triturated with EtOAc (1×5 mL). The resulting solid was filtered through a medium fritted glass funnel, and collected to afford the title compound (37 mg). LC-MS (ES) m/z=446 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 3.10-3.17 (m, 2H), 3.81 (t, J=9.6 Hz, 1H), 4.12 (d, J=10.4 Hz, 1H), 4.34 (d, J=12.0 Hz, 1H), 4.82-4.84 (m, 2H), 5.39 (s, 2H), 6.23 (s, 2H), 6.71 (s, 1H), 7.02-7.09 (m, 1H), 7.25 (d, J=8.8 Hz, 0.5H), 7.41-7.49 (m, 1H), 7.61 (d, J=9.6 Hz, 1.5H), 7.71 (d, J=8.0 Hz, 1H), 7.98 (s, 1H), 11.53 (s, 1H), 12.7 (bs, 1H).

Provenance & Evidence