Citric Acid → 4-Isopropylthiazole-2-carboxylic acid (6-carbamoyl-3-methoxy-2-methyl-phenyl)-amide

HRID 1443451Notes

Reaction equation

HRID 1443451 reaction equation
[NH2:1][C:2]1[C:10]([CH3:11])=[C:9]([O:12][CH3:13])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[CH:14]([C:17]1[N:18]=[C:19]([C:22](O)=[O:23])[S:20][CH:21]=1)([CH3:16])[CH3:15].CCN=C=NCCCN(C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[C:4]([C:3]1[C:2]([NH:1][C:22]([C:19]2[S:20][CH:21]=[C:17]([CH:14]([CH3:16])[CH3:15])[N:18]=2)=[O:23])=[C:10]([CH3:11])[C:9]([O:12][CH3:13])=[CH:8][CH:7]=1)(=[O:5])[NH2:6]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 224993072-Thiazolecarboxylic acid, 4-(1-methylethyl)-HCID 591654352-Amino-4-methoxy-3-methylbenzamide

Product 1

HCID 591654334-Isopropylthiazole-2-carboxylic acid (6-carbamoyl-3-methoxy-2-methyl-phenyl)-amideYield 84.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 2-amino-4-methoxy-3-methyl-benzamide (2.0 g, 11 mmol), 4-isopropyl-thiazole-2-carboxylic acid (2.4 g, 14 mmol) and Hobt-hydrate (2.2 g, 14 mmol) in dry DMF (80 ml) was added EDAC (2.88 g, 15 mmol) and TEA (2.1 ml, 15 mmol) and the mixture was stirred overnight. A 5% aqueous solution of citric acid was added and the mixture was extracted three times with ethyl acetate. The organic phase was washed with saturated sodium hydrogen carbonate solution (two times) and brine, dried with sodium sulfate and evaporated under reduced pressure which gave the title compound (3.1 g).

Workup

  1. extractionthe mixture was extracted three times with ethyl acetate
  2. washThe organic phase was washed with saturated sodium hydrogen carbonate solution (two times) and brine
  3. dry with materialdried with sodium sulfate
  4. customevaporated under reduced pressure which

Sources & evidence

ORD record
ord-542fc29d09fe46cdb748c39644f20bb9
Source dataset
uspto-grants-2010_02
Patent number
US07659245B2

Reaction notes

Loading…