Triethylamine → HCID 10281712, compound

HRID 412365Notes

Reaction equation

HRID 412365 reaction equation
C(N(CC)CC)C.Cl.[C:9](Cl)(=[O:16])[C:10]1[CH:15]=[CH:14][N:13]=[CH: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][N:13]=[CH: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 12262826Isonicotinoyl chloride hydrochlorideHCID 865877685-[4-[6-(4-aminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride

Product 1

HCID 10281712HCID 10281712, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A reaction was conducted by a similar procedure to that described in Example 52 using triethylamine (0.54 ml), isonicotinoyl chloride hydrochloride (284 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 (306 mg, pale yellow powder, mp 222° C. (dec)).

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-74460417b96b44a1b7bc1391991fc3c9
Source dataset
uspto-grants-2003_05
Patent number
US06562849B1

Reaction notes

Loading…