3,5-Difluorobenzoyl chloride → N-[5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-yl]-3,5-difluoro-benzamide

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Reaction Steps

A procedure similar to that in Example 4 was used. 5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-ylamine prepared in Example 1 and 3,5-difluorobenzoyl chloride prepared in the step 1 were used as starting materials, allowed to react at room temperature overnight, followed by post-treatment to obtain a crude product, which was purified by a silica gel column chromatography eluted with a gradient of dichloromethane and ethyl acetate (20:1-10:1) to obtain a product as a white solid in a yield of 59.1%, mp: 154-155└. 1H-NMR (CDCl3, 400 MHz) δ: 3.77 (3H, s, OCH3), 4.23 (2H, s, CH2), 6.72 (2H, d, J=8.44 Hz, ArH), 6.82 (1H, t, 3JFH=8.40 Hz, ArH), 7.17˜7.37 (9H, m, ArH), 11.97 (1H, br, CONH); EI-MS m/e (%): 436.1 (M+, 100), 141.0 (36); HREI-MS Calcd. for C24H18F2N2O2S: 436.1057. found: 436.1053. Anal. Calcd. for C24H18F2N2O2S: C, 66.04; H, 4.16; N, 6.42. found: C, 66.02; H, 4.08; N, 6.44.

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