Benzeneacetic acid, 4-ethoxy- → methyl [1-(cyclopropylmethyl)-2-[(4-ethoxyphenyl)methyl]-1H-benzimidazol-5-yl]carbamate

Participants

Reaction Steps

Following general procedure 13B: Methyl 3-amino-4-[(cyclopropylmethyl)amino]-phenylcarbamate (4.0 g, 17.0 mmol), DIPEA (5 mL), 4-ethoxyphenylacetic acid (3.06 g, 17.0 mmol) and HATU (7.10 g, 18.7 mmol) were combined. The desired product (3.34 g, 52%) precipitated out of the reaction mixture. 1HNMR (CDCl3): δ 7.65 (d, J=2.0 Hz, 1H), 7.37 (br., 1H), 7.26 (d, J=4 Hz), 7.12 (d, J=9.0 Hz, 2H), 6.81 (d, J=9.0 Hz, 2H), 6.74 (br., 1H), 4.25 (s, 2H), 3.98 (q, J=7.4 Hz, 2H), 3.87 (d, J=7.2 Hz, 2H), 3.79 (s, 3H), 1.38 (t, J=7.4 Hz, 3H), 1.05–0.97 (m, 1H), 0.52–0.47 (m, 2H), 0.25–0.20 (m, 2H). MS (ESI) (M+H)+=380.

Provenance & Evidence