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

Participants

Reaction Steps

A procedure similar to that in Example 4 was used. 4-(4-fluoro-phenyl)-5-(4-nitro-benzyl)-thiazol-2-ylamine prepared in Example 9 and 3,5-difluorobenzoyl chloride prepared in the step 1 of Example 16 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 58.0%, mp: 216-218 └. 1H-NMR (DMSO-d6, 400 MHz) δ: 4.44 (2H, s, CH2), 7.30 (2H, t, 3JFH=3JHH=8.96 Hz, ArH), 7.51 (2H, d, J=8.68 Hz, ArH), 7.30 (1H, t, 3JFH=9.00 Hz, ArH), 7.68 (2H, dd, 3JHH=8.68 Hz, 4JFH=5.60 Hz, ArH), 7.30 (2H, d, 3JFH=6.16 Hz, ArH), 8.20 (2H, d, J=8.68 Hz, ArH), 12.95 (1H, br, CONH); EI-MS m/e (%): 469.1 (M+, 77), 141.1 (100); HREI-MS Calcd. for C23H14F3N3O3S: 469.0708. found: 469.0710. Anal. Calcd. for C23H14F3N3O3S: C, 58.85; H, 3.01; N, 8.95. found: C, 58.42; H, 2.64; N, 8.80.

Provenance & Evidence