Veratroyl chloride → HCID 86636629, 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 21 and 3,4-dimethoxy-benzoyl 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 eluted with a gradient of dichloromethane and ethyl acetate (100:0-10:1) to obtain a product as a white solid in a yield of 69.1%, mp: 140-142 └. 1H-NMR (CDCl3, 400 MHz) δ: 3.80 (3H, s, OCH3), 3.84 (3H, s, OCH3), 3.91 (3H, s, OCH3), 4.18 (2H, s, CH2), 6.79 (1H, d, J=8.68 Hz, ArH), 6.82 (2H, d, J=8.68 Hz, ArH), 7.00 (2H, t, 3JFH=3JHH=8.68 Hz, ArH), 7.21 (2H, dd, 3JHH=8.12 Hz, 4JFH=5.32 Hz, ArH), 7.35 (4H, d, J=9.28 Hz, ArH), 11.00 (1H, br, CONH, exchangable); EI-MS m/e (%): 478.2 (M+, 88), 165.0 (100); HREI-MS Calcd. for C26H23FN2O4S: 478.1363. found: 478.1361. Anal. Calcd. for C26H23FN2O4S: C, 65.26; H, 4.84; N, 5.85. found: C, 65.11; H, 4.68; N, 5.96.

Provenance & Evidence