Hydrochloric Acid → HCID 178461990, compound

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 4-(5-methyl-4-oxo-2-((S)-1 -(2-(trifluoromethyl)phenyl) ethylamino)-4,5-dihydrothiazol-5-yl)benzonitrile (0.080 g, 0.20 mmol), prepared according to Example 1, and potassium hydroxide (0.14 g, 2.6 mmol) and t-BuOH (2 mL) was gradually heated to 85° C. After 1 h, 2N HCl was added to the reaction mixture until the pH reached 7-8. The reaction mixture was extracted with CH2Cl2 three times (50 mL). The organic phase was dried over Na2SO4, concentrated in vacuo. The crude product was purified by preparative TLC: 10% MeOH—CH2Cl2. The product (3a) was obtained as a white solid. MS (ESI, pos. ion) m/z: 422 (M+1), 420 (M-1). 1H NMR (CDCl3, 400 MHz): δ1.73-1.77 (m, 3H), 1.98, 2.08 (s, 3H), 5.04 (q, J=8 Hz, 1H), 6.17-6.39 (m, 2H), 7.36-7.42 (m, 2H), 7.52-7.75 (m 4H), 7.80-7.86 (m, 2H).

Provenance & Evidence