1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 69374413, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 264 mg (1 mmol.) of 3-(1H-pyrrolo[2,3-b]pyridin-3-yl)-2-phenyl-2-propenoic acid in 1.5 ml of THFd and 3 ml of DMFd was added 350 μl of N,N,-diisopropylethylamine and 154 mg (1.4 mmol.) of N-hydroxybenzotriazole ammonium salt. The obtained mixture was cooled to −20° C. and 266 mg (1.4 mmol.) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide were added. The reaction mixture was stirred for 2 hours at −20° C. and then warmed to room temperature. After additional 12 hours, the organic layer was diluted with dichloromethane, washed with saturated sodium bicarbonate, brine, dried over sodium sulphate and evaporated. The residual solid was triturated with EtOAc to afford 76 mg of the title compound as a white solid (yield 29%) m.p. 222-224° C. 1H-NMR (DMSO-d6) δ ppm: 11.79 (s, 1H, NH pyrrole); 8.19 (dd, 1H, pyridine); 7.82 (dd, 1H, pyridine); 7.76 (s, 1H, CH═C); 7.2-7.5 (m, 5H, ph); 7.04 (dd, 1H, pyridine); 6.3 (d, 1H, pyrrole); 7.1 (s, 1H, CONH2); 6.7 (s, 1H, CONH2). (M+H)+=264

Provenance & Evidence