Potassium Bicarbonate → N-benzenesulfonyl-4-acetylamino-3-(4-benzyloxybenzylamino)benzamide

HRID 276058Notes

Reaction equation

[K].[C:2]1([S:8]([NH:11][C:12](=[O:24])[C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:22])[CH3:21])=[C:15]([NH2:23])[CH:14]=2)(=[O:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:25]([O:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37]Br)=[CH:35][CH:34]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(=O)([O-])O.[K+]>CN(C)C=O>[C:2]1([S:8]([NH:11][C:12](=[O:24])[C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:22])[CH3:21])=[C:15]([NH:23][CH2:37][C:36]3[CH:39]=[CH:40][C:33]([O:32][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[CH:34][CH:35]=3)[CH:14]=2)(=[O:9])=[O:10])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture containing 0.500 g of N-benzenesulfonyl-3-amino-4-acetylaminobenzamide potassium salt, 0.470 g of 4-benzyloxybenzyl bromide, 0.925 g of a 20% potassium hydrogencarbonate aqueous solution and 3 ml of N,N-dimethylformamide was stirred at 90° C. for 1 hour. The reaction solution was concentrated, and was purified through silica-gel column chromatography (eluent: a mixture of ethyl acetate and methanol at a ratio of 9:1) to obtain crude N-benzenesulfonyl-4-acetylamino-3-(4-benzyloxybenzylamino)benzamide. This crude product was cyclized in the same manner as in Example 183 to give 0.160 g of 6-benzenesulfonylcarbamoyl-1-(4-benzyloxybenzyl)-2-methylbenzimidazole (251).

Workup

concentrationThe reaction solution was concentrated
customwas purified through silica-gel column chromatography (eluent
additiona mixture of ethyl acetate and methanol at a ratio of 9:1)

Sources & evidence

ORD record: ord-ad70cb05a23e43eca8c9b0b8efedb81e
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06352985B1

Reaction notes

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