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

HRID 1694384Notes

Reaction equation

[F:1][C:2]([F:36])([F:35])[C:3]1[CH:34]=[CH:33][C:6]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[C:17]([NH:19][C:20]3([C:23]4[CH:32]=[CH:31][C:26]([C:27]([O:29]C)=[O:28])=[CH:25][CH:24]=4)[CH2:22][CH2:21]3)=[O:18])[CH:10]=[CH:9]2)=[CH:5][CH:4]=1.O>C1COCC1.CO.[OH-].[K+]>[F:36][C:2]([F:1])([F:35])[C:3]1[CH:34]=[CH:33][C:6]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[C:17]([NH:19][C:20]3([C:23]4[CH:24]=[CH:25][C:26]([C:27]([OH:29])=[O:28])=[CH:31][CH:32]=4)[CH2:21][CH2:22]3)=[O:18])[CH:10]=[CH:9]2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 50 °C

Procedure

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).

Workup

temperatureAfter cooling to RT
customthe organic solvents removed
filtrationthe resulting solid was filtered
washwashed with water

Sources & evidence

ORD record: ord-782844eed5ab494da0f92e2b65bc0b02
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158671B2

Reaction notes

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