Water → 4-(1-(1-(4-(trifluoromethyl)benzyl)-1H-indole-7-carboxamido)cyclopropyl)benzoic acid

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Reaction Conditions

Reaction Steps

Methyl 4-{1-[({1-[4-(trifluoromethyl)benzyl]-1H-indol-7-yl}carbonyl)amino]cyclopropyl}benzoate (27 g, 55 mmol) was dissolved in 549 ml of THF 549 ml of MeOH and 249 ml of a 2M solution of KOH. The mixture was heated at 50° C. for 2 h. After cooling to RT, 200 ml of water was added and the organic solvents removed. The solution was acidified to pH 1-1.5 with 3N HCl and the resulting solid was filtered and washed with water. 1H NMR (500 MHz, DMSO-d6): δ 12.80 (bs, 1H), 9.15 (s, 1H), 7.80 (d, 3H), 7.60 (d, 2H), 7.50 (d, 1H), 7.40 (d, 1H), 7.25-7.11 (m, 3H), 6.90 (d, 2H), 6.65 (d, 1H), 5.70 (s, 2H), 1.15 (m, 2H), 0.90 (m, 2H). MS−ESI (477.4).

Provenance & Evidence