1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 68775300, compound

Participants

Reaction Conditions

Reaction Steps

1-[1-(3-Amino-1-methyl-propyl)-piperidin-4-yl]-3-methoxy-1-thiophen-3-ylmethyl-urea (0.150 g, 0.44 mmol), EDCI (0.093 g, 0.48 mmol) and HOBt (0.066 g, 0.48 mmol) were combined in DMF (8 ml) to give a pale yellow solution. To this solution was added 6-cyano-2,4-dimethyl-nicotinic acid (0.091 g, 0.48 mmol) followed by DIPEA (126 μL, 0.66 mmol) and the resulting mixture was stirred at 25° C. for 16 h. Standard workup according to general procedure E gave the crude product as a tan oil. Purification by column chromatography on silica gel (Et2O:MeOH:NH4OH, 90:8:2, v/v/v) afforded 6-cyano-2,4-dimethyl-N-{3-[4-(3-methyl-1-thiophen-3-ylmethyl-ureido)-piperidin-1-yl]-butyl}-nicotinamide (0.170 g, 77%) as a white foam. 1H NMR (CDCl3) δ 0.95 (m, 1H), 1.03 (d+m, 4H), 1.48 (m, 1H), 1.56-1.73 (m, 5H), 2.22 (br t, 1H), 2.32 (s, 3H), 2.54 (s, 3H), 2.58 (br t, 1H), 2.71-2.85 (m, 3H), 3.31 (m, 1H), 3.62 (s, 1H), 3.66 (m, 1H), 3.75 (s, 2H), 3.86 (m, 1H), 4.21 (m, 1H), 7.00 (m, 2H), 7.14 (s, 1H), 7.21 (s, 1H), 7.41 (m, 1H), 8.75 (br d, 1H); ES-MS m/z 499 (M+H).

Provenance & Evidence