1,2-Dichloroethane → N-(1-Ethyl-3-methyl-1H-pyrazol-4-yl)-2-oxo-2-phenyl-N-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-acetamide

HRID 1094393Notes

Reaction equation

HRID 1094393 reaction equation
[CH2:1]([N:3]1[CH:7]=[C:6]([NH:8][CH2:9][CH2:10][C:11]2[CH:12]=[N:13][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:16]=2)[C:5]([CH3:21])=[N:4]1)[CH3:2].[C:22]([C:30](O)=[O:31])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(Cl)CCl>C(Cl)Cl>[CH2:1]([N:3]1[CH:7]=[C:6]([N:8]([CH2:9][CH2:10][C:11]2[CH:12]=[N:13][C:14]([C:17]([F:20])([F:18])[F:19])=[CH:15][CH:16]=2)[C:30](=[O:31])[C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:5]([CH3:21])=[N:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 11915Phenylglyoxylic AcidHCID 58007521(1-Ethyl-3-methyl-1H-pyrazol-4-yl)-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-amine

Product 1

HCID 58007515N-(1-Ethyl-3-methyl-1H-pyrazol-4-yl)-2-oxo-2-phenyl-N-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-acetamideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1-ethyl-3-methyl-1H-pyrazol-4-yl)-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-amine (100 mg) in CH2Cl2 (5 mL) was added under a nitrogen atmosphere at 0° C. benzoyl formic acid (1.1 eq., commercially available) and EDC (1.1 eq). After stirring for 12 h a rt, the mixture was washed with aqueous Na2CO3 (saturated, 2.5 mL) and water (2.5 mL), the combined aqueous layers were extracted with CH2Cl2 (3×2.5 mL) and the combined organic layers dried over sodium sulfate. Concentration afforded the title compound (161 mg, >100%) as a light yellow oil which was used without further purification for the next step. MS m/e: 431.2 [M+H]+.

Workup

  1. washthe mixture was washed with aqueous Na2CO3 (saturated, 2.5 mL) and water (2.5 mL)
  2. extractionthe combined aqueous layers were extracted with CH2Cl2 (3×2.5 mL)
  3. dry with materialthe combined organic layers dried over sodium sulfate
  4. concentrationConcentration

Sources & evidence

ORD record
ord-1e65fc8c50a943ebb2b602ed0e100194
Source dataset
uspto-grants-2012_03
Patent number
US08133909B2

Reaction notes

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