Citric Acid → HCID 59165472, compound

HRID 1443426Notes

Reaction equation

HRID 1443426 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[O:8])=[C:5]([NH2:12])[CH:4]=1.[CH:13]([C:16]1[N:17]=[C:18]([C:21](O)=[O:22])[S:19][CH:20]=1)([CH3:15])[CH3:14].CCN=C=NCCCN(C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[C:7]([C:6]1[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[NH:12][C:21]([C:18]1[S:19][CH:20]=[C:16]([CH:13]([CH3:15])[CH3:14])[N:17]=1)=[O:22])(=[O:8])[NH2:9]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 140230022-Amino-4-methoxybenzamideHCID 224993072-Thiazolecarboxylic acid, 4-(1-methylethyl)-

Product 1

HCID 59165472HCID 59165472, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cooled solution of 4-methoxy-2-aminobenzamide (5.6 g, 33.7 mmol), 4-isopropyl-thiazole-2-carboxlic acid (7.1 g, 42 mmol) and Hobt-hydrate (6.4 g, 42 mmol) in DMF (150 ml) was added EDAC (8.6 g, 45 mmol) and TEA (6.4 ml, 45 mmol) and the mixture was stirred overnight at room temperature. A 2.5% aqueous solution of citric acid (600 ml) was added and the mixture was extracted three times with ethyl acetate. The organic phase was washed with brine and saturated sodium hydrogencarbonate. The solution was dried over sodium sulfate and evaporated under reduced pressure.

Workup

  1. extractionthe mixture was extracted three times with ethyl acetate
  2. washThe organic phase was washed with brine and saturated sodium hydrogencarbonate
  3. dry with materialThe solution was dried over sodium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-143c54aa5eca4f4c9308e9509ca070fe
Source dataset
uspto-grants-2010_02
Patent number
US07659245B2

Reaction notes

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