Triethylamine → HCID 18537619, compound

HRID 2303832Notes

Reaction equation

HRID 2303832 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:36]=[CH:35][C:7]([O:8][C:9]2[CH:10]=[CH:11][C:12]3[N:16]=[C:15]([CH2:17][O:18][C:19]4[CH:32]=[CH:31][C:22]([CH2:23][CH:24]5[S:28][C:27](=[O:29])[NH:26][C:25]5=[O:30])=[CH:21][CH:20]=4)[N:14]([CH3:33])[C:13]=3[CH:34]=2)=[CH:6][CH:5]=1.[F:37][C:38]1[CH:46]=[C:45]([F:47])[CH:44]=[CH:43][C:39]=1[C:40](Cl)=[O:41].C(N(CC)CC)C>CN(C)C=O>[F:37][C:38]1[CH:46]=[C:45]([F:47])[CH:44]=[CH:43][C:39]=1[C:40]([NH:3][C:4]1[CH:36]=[CH:35][C:7]([O:8][C:9]2[CH:10]=[CH:11][C:12]3[N:16]=[C:15]([CH2:17][O:18][C:19]4[CH:32]=[CH:31][C:22]([CH2:23][CH:24]5[S:28][C:27](=[O:29])[NH:26][C:25]5=[O:30])=[CH:21][CH:20]=4)[N:14]([CH3:33])[C:13]=3[CH:34]=2)=[CH:6][CH:5]=1)=[O:41]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5880812,4-Difluorobenzoyl chlorideHCID 865877685-[4-[6-(4-aminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride

Product 1

HCID 18537619HCID 18537619, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a similar manner to that described in Example 47, a reaction was carried out using 5-{4-[6-(4-aminophenoxy)-1-methyl-1H-benzimidazole-2-ylmethoxy]benzyl}thiazolidine-2,4-dione dihydrochloride (400 mg), 2,4-difluorobenzoylchloride (141 mg), triethylamine (232 mg) and anhydrous N,N-dimethylformamide (8 ml) and the reaction mixture was purified to give the title compound (251 mg).

Workup

  1. customthe reaction mixture was purified

Sources & evidence

ORD record
ord-213f8a704c2944a58de39bda529a1b2d
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

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