Hydrazine hydrate (1:1) → HCID 58504623, compound

Participants

Reaction Conditions

Reaction Steps

2-Fluoro-4-{2-(methylamino)-6-[(2S)-2-(trifluoromethyl)-1-pyrrolidinyl]-4-pyrimidinyl}benzonitrile (166 mg, 0.454 mmol) was dissolved in ethanol (3 mL) in a 5 mL sealable vial. Hydrazine monohydrate (0.668 mL, 13.63 mmol) was added, the vial was capped, and the reaction was heated at 100° C. overnight. The reaction was concentrated, dissolved in 2 mL of DMSO and purified in 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, 1% CH3CN/H2O, 0.1% TFA to 42% 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, then 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 (91 mg) as a light yellow solid. LC-MS (ES) m/z=377 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 2.01-2.22 (m, 4H), 2.85 (d, J=4.3 Hz, 3H), 3.48-3.61 (m, 1H), 3.68 (dt, J=10.1, 5.1 Hz, 1H), 5.14 (t, 1H), 5.40 (bs, 2H), 6.50 (bs, 1H), 6.68 (bs, 1H), 7.59 (d, J=8.3 Hz, 1H), 7.73 (d, J=8.3 Hz, 1H), 7.97 (bs, 1H), 11.54 (s, 1H).

Provenance & Evidence