Citric Acid → HCID 59165472, compound

HRID 643844Notes

Reaction equation

HRID 643844 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-isopropylthiazole-2-carboxylic 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 sulphate and evaporated under reduced pressure. Yield: 9.0 g, 91%.

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 sulphate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-4c97e6866e684295a2504ca4c6f59b50
Source dataset
uspto-grants-2010_04
Patent number
US07700552B2

Reaction notes

Loading…