Hydrochloric Acid → 4-[6-(N-cyclopentylmethylcarbamoyl)-3-[2-(pyrrolidinocarbonyl)ethyl]indol1-ylmethyl]-3-methoxybenzoic acid

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Reaction Steps

A solution of 4-[6-(N-cyclopentylmethylcarbamoyl)-3-(2-methoxycarbonylethyl)indol-1-ylmethyl]-3-methoxybenzoic acid (0.84 g) (prepared as described in Example 1, parts (a) through (i)) and 4-(dimethylamino)pyridine (0.21 g) in pyrrolidine (5 ml) was heated at 80° for 48 hours under a nitrogen atmosphere. The reaction was diluted with water and acidified with 10% (v/v) hydrochloric acid. The resultant precipitate was collected by filtration and washed with water to give 4-[6-(N-cyclopentylmethylcarbamoyl)-3-[2-(pyrrolidinocarbonyl)ethyl]indol1-ylmethyl]-3-methoxybenzoic acid as a white powder (0.77 g, 85%): partial NMR (80 MHz, DMSO-d6 : 1.1-2.0 (m, 12H), 2.1(m, 1H, NHCH2CH), 3.9(s, 3H, OCH3), 6.7(d, 1H, Ar), 7.3(s, 1H, H2 -indole), 8.3(t,1H, NH).

Provenance & Evidence