Water → 6-[[(4-Fluorophenyl)sulfonyl][1,2-diphenyl-1H-benzimidazol-5-yl]amino]hexanoic acid methyl ester

HRID 1242223Notes

Reaction equation

[C:1]1([N:7]2[C:11]3[CH:12]=[CH:13][C:14]([NH:16][S:17]([C:20]4[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=4)(=[O:19])=[O:18])=[CH:15][C:10]=3[N:9]=[C:8]2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:35][O:36][C:37](=[O:44])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]Br.O>CN(C)C=O>[CH3:35][O:36][C:37](=[O:44])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][N:16]([S:17]([C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)(=[O:19])=[O:18])[C:14]1[CH:13]=[CH:12][C:11]2[N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:8]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[N:9][C:10]=2[CH:15]=1

Participants

Conditions

Temperature: 20 °C

Procedure

150 mg of N-(1,2-diphenyl-1H-benzimidazol-5-yl)-4-fluorobenzenesulfonamide was suspended in 0.5 ml of N,N-dimethylformamide, mixed with 12 mg of sodium hydride and stirred for 30 minutes at 20° C. 98 mg of 6-bromohexanoic acid methyl ester was added, allowed to stir for 15 hours, mixed with water, extracted three times with ethyl acetate, the extracts were dried on sodium sulfate, concentrated by evaporation in a vacuum, and the residue was chromatographed on silica gel.

Workup

stirringto stir for 15 hours
extractionextracted three times with ethyl acetate
customthe extracts were dried on sodium sulfate
concentrationconcentrated by evaporation in a vacuum
customthe residue was chromatographed on silica gel

Sources & evidence

ORD record: ord-ac01308a895d402e863b59cee5085af6
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115645B2

Reaction notes

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