Fumaric Acid → 3-Cyclohexyl-5-ethoxy-1,3-dihydro-1-[2-methoxy-4-[N-(2-dimethylamino-1,1-dimethylethyl)carbamoyl]benzenesulfonyl]-2H-benzimidazol-2-one fumarate

HRID 1081517Notes

Reaction equation

HRID 1081517 reaction equation
[CH:1]1([N:7]2[C:11]3[CH:12]=[C:13]([O:16][CH2:17][CH3:18])[CH:14]=[CH:15][C:10]=3[N:9]([S:19]([C:22]3[CH:27]=[CH:26][C:25]([C:28](=[O:37])[NH:29][C:30]([CH3:36])([CH3:35])[CH2:31][N:32]([CH3:34])[CH3:33])=[CH:24][C:23]=3[O:38][CH3:39])(=[O:21])=[O:20])[C:8]2=[O:40])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:41]([OH:48])(=[O:47])/[CH:42]=[CH:43]/[C:44]([OH:46])=[O:45]>CC(C)=O>[C:41]([OH:48])(=[O:47])/[CH:42]=[CH:43]/[C:44]([OH:46])=[O:45].[CH:1]1([N:7]2[C:11]3[CH:12]=[C:13]([O:16][CH2:17][CH3:18])[CH:14]=[CH:15][C:10]=3[N:9]([S:19]([C:22]3[CH:27]=[CH:26][C:25]([C:28](=[O:37])[NH:29][C:30]([CH3:35])([CH3:36])[CH2:31][N:32]([CH3:34])[CH3:33])=[CH:24][C:23]=3[O:38][CH3:39])(=[O:20])=[O:21])[C:8]2=[O:40])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 233642313-Cyclohexyl-5-ethoxy-1,3-dihydro-1-[2-methoxy-4-[N-(2-dimethylamino-1,1-dimethylethyl)carbamoyl]benzenesulfonyl]-2H-benzimidazol-2-one

Product 1

HCID 233642373-Cyclohexyl-5-ethoxy-1,3-dihydro-1-[2-methoxy-4-[N-(2-dimethylamino-1,1-dimethylethyl)carbamoyl]benzenesulfonyl]-2H-benzimidazol-2-one fumarateYield 43.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 0.48 g of the compound obtained in EXAMPLE 115, 0.05 g of fumaric acid and 15 ml of acetone is refluxed for 5 minutes. The reaction mixture is concentrated under vacuum to give 0.13 g of the expected product after crystallization from ether. M.p.=135° C.

Workup

  1. temperatureis refluxed for 5 minutes
  2. concentrationThe reaction mixture is concentrated under vacuum

Sources & evidence

ORD record
ord-df93ffa7f877426e875d56f2fd21cad3
Source dataset
uspto-grants-1996_12
Patent number
US05585394

Reaction notes

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