Hydrazine hydrate (1:1) → HCID 58504440, compound

Participants

Reaction Conditions

Reaction Steps

To N-{(3S,6R)-1-[2-amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-6-methyl-3-piperidinyl}benzamide (101 mg, 0.234 mmol) in ethanol (2 mL) into a 5 mL sealable vial was added hydrazine monohydrate (0.22 mL, 7.02 mmol), and the reaction was capped and heat overnight at 100° C. The reaction was concentrated, re dissolved in 1 mL of DMSO, and purified on HPLC (HPLC condition: open-access Gilson using Unipoint software with a Varian Polaris 5u C18(2) 100A, 50×30.00 mm 5 micron. 10-minute run (30 ml/min, 15% CH3CN/H2O, 0.1% TFA to 40% CH3CN/H2O, 0.1% TFA) with UV detection at 254 nm). Product fractions were combined and the volume was reduced to remove most of the CH3CN. To the resulting aqueous mixture was added sat. aqueous NaHCO3, and then it was extracted with EtOAc (3×15 mL). The organic was washed with brine, dried over MgSO4, filtered and concentrated to afford the title compound (20 mg) as a light yellow solid. LC-MS (ES) m/z=443 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.19 (d, J=6.8 Hz, 3H), 1.24 (s, 1H), 1.66-1.93 (m, 5H), 2.54 (s, 1H), 3.89 (d, J=4.0 Hz, 1H), 5.39 (s, 2H), 6.13 (bs, 1H), 6.62 (s, 1H), 7.47-7.59 (m, 5H), 7.71 (d, J=8.6 Hz, 1H), 7.90 (d, J=7.1 Hz, 2H), 7.94 (s, 1H), 8.43 (d, J=8.1 Hz, 1H), 11.51 (bs, 1H).

Provenance & Evidence