Hydrazine hydrate (1:1) → HCID 58504595, compound

Participants

Reaction Conditions

Reaction Steps

Into a 5 mL sealable vial were added 4-{2-amino-6-[(3R)-3-(2-oxo-1,3-oxazolidin-3-yl)-1-piperidinyl]-4-pyrimidinyl}-2-fluorobenzonitrile (83 mg, 0.217 mmol) and ethanol (3 mL) followed by hydrazine monohydrate (0.319 mL, 6.51 mmol). The reaction vial was capped and was 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 25% 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 and then extracted with EtOAc (5×100 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 (37 mg) as a light yellow solid. LC-MS (ES) m/z=395 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.45-1.58 (m, 1H), 1.68-1.89 (m, 3H), 2.82 (t, J=11.6 Hz, 1H), 2.99 (t, J=11.8 Hz, 1H), 3.54 (ddd, J=11.1, 7.0, 4.2 Hz, 1H), 3.60 (dd, J=9.6, 8.6 Hz, 2H), 4.29 (td, J=8.0, 2.2 Hz, 2H), 4.40 (dd, 2H), 5.38 (s, 2H), 6.14 (bs, 2H), 6.63 (s, 1H), 7.57 (dd, J=8.3, 1.3 Hz, 1H), 7.71 (d, J=8.3 Hz, 1H), 7.95 (s, 1H), 11.52 (s, 1H).

Provenance & Evidence