Ammonia → 3-Acetyl-1-(2-chlorobenzyl)-2-propylindole-6-carboxamide

HRID 1108716Notes

Reaction equation

[C:1]([C:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13](O)=[O:14])=[CH:10][CH:11]=2)[N:6]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])[C:5]=1[CH2:24][CH2:25][CH3:26])(=[O:3])[CH3:2].O[N:28]1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.N>CN(C)C=O.C(OCC)(=O)C.CO>[C:1]([C:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([NH2:28])=[O:14])=[CH:10][CH:11]=2)[N:6]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])[C:5]=1[CH2:24][CH2:25][CH3:26])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 2 °C

Procedure

To a solution of 3-acetyl-1-(2-chlorobenzyl)-2-propylindole-6-carboxylic acid (74 mg) in dimethylformamide (2 ml) were added 1-hydroxybenzotriazole (38 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (98 mg) and 3N methanol solution of ammonia (0.5 ml). After stirred at 2° C. for 14 hours, the resulting mixture was diluted with ethyl acetate. The organic phase was washed successively with 1N hydrochloric acid, water, aqueous sodium bicarbonate and brine, dried over sodium sulfate and evaporated in vacuo. The residue was triturated with isopropyl ether to give 3-acetyl-1-(2-chlorobenzyl)-2-propylindole-6-carboxamide (67 mg) as colorless crystals.

Workup

washThe organic phase was washed successively with 1N hydrochloric acid, water, aqueous sodium bicarbonate and brine
dry with materialdried over sodium sulfate
customevaporated in vacuo
customThe residue was triturated with isopropyl ether

Sources & evidence

ORD record: ord-57ef45dcc37b4e04b55214d198126fe0
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06069156

Reaction notes

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