Hydrazine → HCID 58504628, compound

Participants

Reaction Conditions

Reaction Steps

Into a 5 mL sealable vial was added 1-methylethyl{(3R)-1-[2-amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-3-piperidinyl}carbamate (116 mg, 0.291 mmol) followed by ethanol (3 mL) and hydrazine (0.428 mL, 8.73 mmol). The mixture was then capped and heated at 100° C. overnight. The reaction was concentrated, then dissolved in 2 mL of DMSO and purified on HPLC (HPLC condition: open-access Gilson using Trilution software with a Sunfire 5u C18(2) 100A. 50×30.00 mm 5 micron. 7.3-minute run (47 mL/min, 10% CH3CN/H2O, 0.1% TFA to 35% 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 water left behind was added saturated NaHCO3. It was then extracted with EtOAc (3×15 mL) and the organic fractions were combined and washed with saturated NaCl solution, dried over MgSO4, filtered and concentrated. The product was then transferred to a haystack vial and 1 mL of water was added and freeze dried. LC-MS (ES) m/z=411 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.13 (d, 3H), 1.16 (d, J=6.3 Hz, 3H), 1.39-1.49 (m, 2H), 1.70-1.77 (m, 1H), 1.85-1.93 (m, 1H), 2.87 (bs, 1H), 3.03 (bs, 1H), 4.06-4.16 (m, 1H), 4.28 (bs, 1H), 4.77 (ddd, J=12.51, 6.19, 6.06 Hz, 1H), 5.38 (s, 2H), 6.09 (bs, 2H), 6.56 (s, 1H), 7.16 (d, J=7.6 Hz, 1H), 7.54 (d, J=8.6 Hz, 1H), 7.70 (d, J=8.3 Hz, 1H), 7.92 (s, 1H), 11.52 (s, 1H).

Provenance & Evidence