Hydrazine → HCID 58504405, compound

Participants

Reaction Conditions

Reaction Steps

To N-{(3S,6R)-1-[2-amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-6-methyl-3-piperidinyl}-2-phenylacetamide (105 mg, 0.236 mmol) in ethanol (2 mL) into a 5 mL sealable vial was added hydrazine (0.22 mL, 7.1 mmol), and the reaction was then capped and heated on a hot plate at 100° C. overnight. The reaction was concentrated, then redissolved 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 45% 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, concentrated, and transferred to a haystack vial. Water (1 mL) was added, and the resulting mixture was freeze dried to afford the title compound (44 mg) as a light yellow solid. LC-MS (ES) m/z=457 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.15 (d, J=6.8 Hz, 3H), 1.61-1.76 (m, 4H), 2.57-2.68 (m, 1H), 3.44 (s, 2H), 3.59 (dd, J=7.7, 3.4 Hz, 1H), 4.38-4.84 (m, 2H), 5.38 (s, 2H), 6.11 (bs, 2H), 6.56 (s, 1H), 7.21-7.36 (m, 5H), 7.54 (dd, J=8.6, 1.0 Hz, 1H), 7.71 (d, J=8.3 Hz, 1H), 7.92 (s, 1H), 8.16 (d, J=8.1 Hz, 1H), 11.51 (s, 1H).

Provenance & Evidence