Triethylamine → HCID 86596080, compound

HRID 1823785Notes

Reaction equation

HRID 1823785 reaction equation
[CH2:1]([N:8]1[C:12]2[CH:13]=[C:14]([OH:17])[CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[NH:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:29][C:30]1[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=1.C(N(CC)CC)C>CC(C)=O>[CH2:1]([N:8]1[C:12]2[CH:13]=[C:14]([O:17][S:36]([C:33]3[CH:34]=[CH:35][C:30]([F:29])=[CH:31][CH:32]=3)(=[O:38])=[O:37])[CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[NH:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 22147021HCID 22147021, compound

Product 1

HCID 86596080HCID 86596080, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred solution of 3-benzyl-2-(3,4-dimethoxy-phenylamino)-3H-benzoimidazol-5-ol (141 mg) and 4-fluoro-benzenesulfonyl chloride (190 mg) in acetone (8 ml) was treated with triethylamine (258 μl). After stirring at ambient temperature for 4 hours, the reaction mixture was evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and heptane (1:1, v/v) to give 4-fluoro-benzenesulfonic acid 3-benzyl-2-(3,4-dimethoxy-phenylamino)-3H-benzoimidazol-5-yl ester (157 mg) as a yellow solid. Mass spectrum: 534 [M+H]+, retention time: 3.7 minutes.

Workup

  1. customthe reaction mixture was evaporated
  2. additionThe residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and heptane (1:1

Sources & evidence

ORD record
ord-66d850bb46b640cc8263f814d898806a
Source dataset
uspto-grants-2006_05
Patent number
US07041668B2

Reaction notes

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