Hydrochloric Acid → 4-[6-(N-cyclopentylmethylcarbamoyl)-3-[2-(morpholinocarbonyl)ethyl]indol-1-ylmethyl]-3-methoxybenzoic acid

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Reaction Steps

The starting indole was obtained as follows: A solution of 4-[6-(N-cyclopentylmethylcarbamoyl)-3-(2-methoxycarbonylethyl)indol-1-ylmethyl)]-3-methoxybenzoic acid (0.68g)(prepared as described in Example 1, parts (a) through (i)) and 4-(dimethylamino)pyridine (0.17 g) in morpholine (4 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. The product was purified by recrystallization from ethyl acetate to give 4-[6-(N-cyclopentylmethylcarbamoyl)-3-[2-(morpholinocarbonyl)ethyl]indol-1-ylmethyl]-3-methoxybenzoic acid as a white powder (0.31 g, 41%); partial NMR (80 MHz, CDCl3) 1.2-1.8(m, 9H, cyclopentyl), 2.70(dd, 2H, CH2NH), 3.15(t, 2H, COCH2), 3.2-3.7(m, 8H, morpholino), 3.92(s, 3H, OCH3), 5.35(s, 2H, ArCH2), 6.58(t, 1H, NH), 7.17(d, 1H), 7.9(s, 1H, H7 -indole).

Provenance & Evidence