Hydrazine hydrate (1:1) → HCID 58504537, compound

Participants

Reaction Conditions

Reaction Steps

To N-{(3R)-1-[6-(4-cyano-3-fluorophenyl)-2-(methylamino)-4-pyrimidinyl]-3-piperidinyl}benzamide (83 mg, 0.19 mmol) in ethanol (2 mL) was added hydrazine monohydrate (0.5 mL, 10.2 mmol), and the reaction mixture was stirred overnight at 100° C. into a sealed tube. The solution was poured onto water (˜50 mL) and a precipitate formed. The aqueous mixture was filtered, and the solid was further washed with water. The material was dried under vacuum overnight at 45° C. to afford the title compound (52 mg) as an off-white solid. LC-MS (ES) m/z=443 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.43-1.60 (m, 1H), 1.61-1.75 (m, 1H), 1.76-1.89 (m, 1H), 1.92-2.05 (m, 1H), 2.83 (d, J=4.0 Hz, 3H), 2.91-3.10 (m, 2H), 3.83-3.98 (m, 1H), 4.24-4.57 (m, 2H), 5.38 (s, 2H), 6.45-6.58 (m, 1H), 6.64 (s, 1H), 7.41-7.49 (m, 2H), 7.50-7.56 (m, 1H), 7.59 (d, J=8.6 Hz, 1H), 7.71 (d, J=8.34 Hz, 1H), 7.82-7.90 (m, 2H), 7.98 (bs, 1H), 8.37 (d, J=7.6 Hz, 1H), 11.50 (s, 1H).

Provenance & Evidence