Benzoyl chloride, 3,4,5-trimethoxy- → N-[5-cyclohexylmethyl-4-(4-hydroxy-phenyl)-thiazol-2-yl]-3,4,5-trimethoxy-benzamide

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Reaction Steps

A procedure similar to that in Example 4 was used. 5-cyclohexylmethyl-4-(4-methoxy-phenyl)-thiazol-2-ylamine prepared in Example 47 and 3,4,5-trimethoxy-benzoyl chloride prepared in the step 1 of Example 37 were used as starting materials, allowed to react at room temperature overnight, followed by post-treatment to give a crude product, which was purified by a silica gel column chromatography eluted with a gradient of dichloromethane and ethyl acetate (20:1) to obtain a product as a white solid in a yield of 60.1%, mp: 193-194└. 1H-NMR (CDCl3, 400 MHz) δ: 0.85˜0.98 (2H, m), 1.05˜1.28 (3H, m), 1.58˜1.88 (6H, m), 2.75 (2H, d, J=7.28 Hz, CHCH2Ar), 3.74 (3H, s, OCH3), 3.77 (3H, s, OCH3), 3.79 (3H, s, OCH3), 3.97 (3H, s, OCH3), 6.77 (2H, d, J=8.44 Hz, ArH), 6.98 (2H, s, ArH), 7.29 (2H, d, J=8.44 Hz, ArH); EI-MS m/e (%): 496.1 (M+, 64), 413.1 (48), 195.1 (100); HREI-MS Calcd. for C27H32N2O5S: 496.2032. found: 496.2040. Anal. Calcd. for C27H32N2O5S: C, 65.30; H, 6.49; N, 5.64. found: C, 65.11; H, 6.55; N, 5.70.

Provenance & Evidence