1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Methyl 4-[2-oxo-2-(2-{[3-(trifluoromethyl)phenyl]carbonyl}hydrazino)ethyl]benzoate

HRID 1257476Notes

Reaction equation

HRID 1257476 reaction equation
Cl.[F:2][C:3]([F:15])([F:14])[C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([NH:9][NH2:10])=[O:8].[CH3:16][O:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27](O)=[O:28])=[CH:22][CH:21]=1)=[O:19].CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C)C=O.O.C(N(CC)CC)C>[O:28]=[C:27]([NH:10][NH:9][C:7]([C:6]1[CH:11]=[CH:12][CH:13]=[C:4]([C:3]([F:14])([F:15])[F:2])[CH:5]=1)=[O:8])[CH2:26][C:23]1[CH:24]=[CH:25][C:20]([C:18]([O:17][CH3:16])=[O:19])=[CH:21][CH:22]=1

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 107978792-(4-(Methoxycarbonyl)phenyl)acetic acidHCID 669395863-(Trifluoromethyl)benzohydrazide hydrochloride

Product 1

HCID 66939425Methyl 4-[2-oxo-2-(2-{[3-(trifluoromethyl)phenyl]carbonyl}hydrazino)ethyl]benzoateYield 28.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 3-(trifluoromethyl)benzohydrazide hydrochloride (2.3 g) in N,N-dimethylformamide (20 mL) were added the compound (1.8 g) obtained in Example 206a, N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide (3.50 g), 1-hydroxybenzotriazole (1.25 g) and triethylamine (4.68 g). The reaction mixture was stirred at room temperature overnight, poured into water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and then saturated brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (1.0 g) as a colorless solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate
  3. dry with materialsaturated brine, and dried over sodium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-be4446abfdf74dd9931c7853ed145f36
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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