Phosgene → [3-Methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-[4-methyl-5-(3-trifluoromethyl-benzyl)-thiazol-2-yl]-amine

Participants

Reaction Steps

The title compound was prepared in analogy to example 7 without purification of the intermediate from 161 mg (1 mmol) 3-trifluoromethylaniline and 421 mg (6 mmol) methyl vinylketone. The crude chloroketone was used without further purification in the next step with 53 mg (0.2 mmol) [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea. The crude product was purified on silica gel with methylene chloride/methanol 19/1 yielding 50 mg (55%) [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-[4-methyl-5-(3-trifluoromethyl-benzyl)-thiazol-2-yl]-amine as a brown solid. MS ISP (m/e): 459.1 (100) (M+H)+. 1H NMR (DMSO-D6, 250 MHz): δ (ppm)=10.18 (s, 1H), 7.66-7.53 (m, 7H), 7.23 (s, 1H), 7.01 (s, 1H), 4.11 (s, 2H), 3.77 (s, 3H), 2.25 (s, 3H), 2.14 (s, 3H).

Provenance & Evidence