Hydrazine hydrate (1:1) → HCID 58504424, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of crude N-({(2S,5R)-4-[2-amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-5-methyl-2-morpholinyl}methyl)benzenesulfonamide (0.29 mmol theoretical) and hydrazine monohydrate (0.28 mL, 5.78 mmol) in ethanol (3 mL) was stirred at 100° C. in a sealed tube for 17 hours. The mixture was concentrated in vacuo and the residue was purified on a Gilson reverse phase HPLC (CH3CN/water with 0.1% TFA). The product fractions were combined and concentrated in vacuo, taken up in EtOAc (15 mL) and a little CH3OH, washed with saturated aqueous NaHCO3 (2×10 mL) and brine (10 mL), then dried (Na2SO4), filtered, and concentrated in vacuo to afford the title compound (59 mg) as a pale yellow solid. LC-MS (ES) m/z=495 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.12 (d, J=6.3 Hz, 3H), 2.65-2.80 (m, 1H), 2.86-3.04 (m, 2H), 3.34-3.43 (m, 1H), 3.47-3.59 (m, 1H), 3.65-3.75 (m, 1H), 3.85-4.75 (bs, 2H), 5.39 (s, 2H), 6.13 (s, 2H), 6.52 (s, 1H), 7.56 (dd, J=8.6, 1.0 Hz, 1H), 7.58-7.68 (m, 3H), 7.69-7.74 (m, 1H), 7.85 (dd, J=7.6, 1.7 Hz, 2H), 7.88-7.97 (m, 2H), 11.53 (s, 1H).

Provenance & Evidence