Sodium Hydroxide → HCID 57590768, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl (3R)-3-({4-[6-(3-cyanophenyl)imidazo[2,1-b][1,3]thiazol-5-yl]pyrimidin-2-yl}amino)piperidine-1-carboxylate (0.204 g, 0.407 mmol) in ethanol (5 mL) was added 25% aqueous sodium hydroxide (0.072 mL, 0.448 mmol). The mixture was heated at 75° C. for 20 hours. Solvent was removed to dryness. Residue was taken into dichloromethane (20 mL), washed with water (5 mL), dried over sodium sulfate and concentrated. Product was purified by flash chromatography on silica gel eluting with 5% methanol in dichloromethane to afford 0.175 g (83%) of the title compound as an off-white solid. M.p.=161-165° C. 400 MHz 1H NMR (DMSO-d6 at 60° C.) δ: 8.70 (br. s, 1H), 8.14 (s, 1H), 8.10 (d, J=5.6 Hz, 1H), 7.94 (d, J=8.0 Hz, 1H), 7.72 (d, J=7.6 Hz, 1H). 7.54(t, J=7.6 Hz, 1H), 7.44 (d, J=4.4 Hz, 1H), 7.30-7.14 (bs, 2H), 7.15 (d, J=6.8 Hz, 1H), 6.33 (d, J=5.2 Hz, 1H), 3.96 (bs, 1H), 3.81-3.77 (m, 1H), 3.68 (bs, 1H), 2.94-2.90 (m, 2H), 2.00-1.97 (m, 1H), 1.80-1.77 (m, 1H), 1.59-1.53 (m, 1H), 1.46-1.40 (m, 1H), 1.34 (s, 9H); LCMS: 520 [M+H].

Provenance & Evidence