Ammonia → 184147-65-7

HRID 278104Notes

Reaction equation

[Cl:1][C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14](O)=[O:15])[CH:12]=2)[C:7]([C:17](=[O:21])[CH:18]([CH3:20])[CH3:19])=[C:6]1[CH2:22][CH2:23][CH3:24].O[N:30]1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.N>CN(C)C=O>[Cl:1][C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([NH2:30])=[O:15])[CH:12]=2)[C:7]([C:17](=[O:21])[CH:18]([CH3:20])[CH3:19])=[C:6]1[CH2:22][CH2:23][CH3:24]

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of 1-(2-chlorobenzyl)-3-isobutyryl-2-propylindole-6-carboxylic acid (150 mg) in dimethylformamide (3 ml) were added 1-hydroxybenzotriazole (102 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (109 mg). After stirred at 20° C. over night, the resulting mixture was poured into 28% aqueous ammonia (5 ml). The mixture was partitioned between ethyl acetate and water, and the organic phase was washed with 1N hydrochloric acid and brine, dried over sodium sulfate and evaporated in vacuo. The crystalline residue was recyrystallized from a mixture of ethyl acetate and hexane to give 1-(2-chlorobenzyl)-3-isobutyryl-2-propylindole-6-carboxamide (123 mg) as colorless crystals.

Workup

customThe mixture was partitioned between ethyl acetate and water
washthe organic phase was washed with 1N hydrochloric acid and brine
dry with materialdried over sodium sulfate
customevaporated in vacuo
additionThe crystalline residue was recyrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record: ord-5c884e7bae0f44ee878274aa756da5bb
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06358992B1

Reaction notes

Loading…