4-(2-Amino-1,3-thiazol-4-yl)benzonitrile → N-[4-(4-Cyanophenyl)-1,3-thiazol-2-yl]-6-{(E)-2-[2-(2,2-dimethylpropoxy)-3-methoxyphenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxamide

Participants

Reaction Steps

The title compound was prepared according to the general procedure (Method B) by coupling Intermediate 3 (130 mg, 0.336 mmol) with 4-(2-amino-1,3-thiazol-4-yl)benzonitrile (81 mg, 0.403 mmol) in the presence of EDCI hydrochloride (128 mg, 0.672 mmol) and DMAP (61 mg, 0.504 mmol) in a mixture of DCM and DMF (4:1, 5 mL) to give 27 mg of the product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.02 (s, 9H), 3.57 (s, 2H), 3.80 (s, 3H), 7.00 (d, J=8.4 Hz, 1H), 7.11 (t, J=7.8 Hz, 1H), 7.34 (d, J=7.2 Hz, 1H), 7.40-7.50 (m, 2H), 7.84 (s, 1H), 7.91-7.96 (m, 2H), 7.98-8.05 (m, 1H), 8.10-8.15 (m, 2H), 12.79 (br s, 1H); APCI-MS (m/z) 570.17 (MH)+.

Provenance & Evidence