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

HRID 278102Notes

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: 20 °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 20° 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-c0b02f458486496f8649160bb458f443
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06358992B1

Reaction notes

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