Triethylamine → HCID 9916255, compound

HRID 412366Notes

Reaction equation

HRID 412366 reaction equation
C(N(CC)CC)C.Cl.[C:9](Cl)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[N:12][CH:11]=1.Cl.Cl.[NH2:20][C:21]1[CH:53]=[CH:52][C:24]([O:25][C:26]2[CH:27]=[CH:28][C:29]3[N:33]=[C:32]([CH2:34][O:35][C:36]4[CH:49]=[CH:48][C:39]([CH2:40][CH:41]5[S:45][C:44](=[O:46])[NH:43][C:42]5=[O:47])=[CH:38][CH:37]=4)[N:31]([CH3:50])[C:30]=3[CH:51]=2)=[CH:23][CH:22]=1>CN(C)C=O>[O:46]=[C:44]1[NH:43][C:42](=[O:47])[CH:41]([CH2:40][C:39]2[CH:38]=[CH:37][C:36]([O:35][CH2:34][C:32]3[N:31]([CH3:50])[C:30]4[CH:51]=[C:26]([O:25][C:24]5[CH:52]=[CH:53][C:21]([NH:20][C:9](=[O:16])[C:10]6[CH:15]=[CH:14][CH:13]=[N:12][CH:11]=6)=[CH:22][CH:23]=5)[CH:27]=[CH:28][C:29]=4[N:33]=3)=[CH:49][CH:48]=2)[S:45]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 865877685-[4-[6-(4-aminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride

Product 1

HCID 9916255HCID 9916255, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A reaction was conducted by a similar procedure to that described in Example 52 using triethylamine (0.49 ml), nicotinoyl chloride hydrochloride (195 mg), 5-[4-[6-(4-aminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride (400 mg) and anhydrous N,N-dimethylformamide (8 ml). The reaction mixture was concentrated under reduced pressure. To the residue was added ethyl acetate and water. The precipitate was isolated by filtration to afford the title compound (297 mg, pale yellow powder, mp 213-215° C.).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionTo the residue was added ethyl acetate and water
  3. customThe precipitate was isolated by filtration

Sources & evidence

ORD record
ord-28ce3157eb964046b7455a12adcdfc5f
Source dataset
uspto-grants-2003_05
Patent number
US06562849B1

Reaction notes

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