4-Cyanobenzoyl chloride → HCID 57991633, compound

Participants

Reaction Steps

A procedure similar to that in Example 4 was used. 5-(4-fluoro-benzyl)-4-(4-methoxy-phenyl)-thiazol-2-ylamine prepared in Example 13 and p-cyanobenzoyl chloride prepared in the step 1 of Example 12 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, and recrystallized with petroleum ether and ethyl acetate to obtain a product as a white solid in a yield of 85.9%, mp: 191-192 └. 1H-NMR (CDCl3, 400 MHz) δ: 3.79 (3H, s, OCH3), 4.18 (2H, s, CH2), 6.73 (2H, d, J=8.96 Hz, ArH), 7.03 (2H, t, 3JFH=3JHH=8.68 Hz, ArH), 7.19 (2H, dd, 3JHH=8.96, 4JFH=5.60 Hz, ArH), 7.24 (2H, d, J=8.96 Hz, ArH), 7.53 (2H, d, J=8.40 Hz, ArH), 7.76 (2H, d, J=8.40 Hz, ArH), 11.74 (1H, br, CONH); EI-MS m/e (%): 443.1 (M, 100), 130.0 (48); HREI-MS Calcd. for C25H18FN3O2S: 443.1104. found: 443.1108. Anal. Calcd. for C25H18FN3O2S: C, 67.71; H, 4.09; N, 9.47. found: C, 67.89; H, 3.97; N, 9.42.

Provenance & Evidence