Hydrazine → HCID 58504458, compound

Participants

Reaction Conditions

Reaction Steps

To phenylmethyl{(3S,6R)-1-[2-amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-6-methyl-3-piperidinyl}carbamate (57 mg, 0.124 mmol) in ethanol (3 mL) was added hydrazine (0.182 mL, 3.71 mmol) into a 5 mL sealable vial. The solution was then capped and heated at 100° C. overnight. The reaction was then concentrated, re-dissolved in 2 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, 33% CH3CN/H2O, 0.1% TFA to 58% CH3CN/H2O, 0.1% TFA) with UV detection at 254 nm). Product fractions were combined, and the volume was reduced to remove the CH3CN. To the resulting aqueous mixture was added 5 mL of saturated aqueous NaHCO3, and then extracted 3× with EtOAc. The organics were then combined, washed with brine, dried over MgSO4, filtered and concentrated to afford the title compound (37 mg) as a light yellow solid. LC-MS (ES) m/z=473 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.12 (d, J=6.8 Hz, 3H), 1.66 (m, 4H), 2.67 (dt, J=3.7, 1.8 Hz, 1H), 3.38 (bs, 1H), 4.50 (bs, 1H), 4.73 (bs, 1H), 5.06 (d, J=5.3 Hz, 2H), 5.39 (s, 2H), 6.04-6.20 (bs, 2H), 6.58 (bs, 1H), 7.30-7.46 (m, 6H), 7.55 (d, J=8.3 Hz, 1H), 7.71 (d, J=8.3 Hz, 1H), 7.93 (s, 1H), 11.52 (bs, 1H).

Provenance & Evidence