Sodium hydride → 1-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-4-(2,2,2-trifluoro-ethoxy)-1H-pyrazole-3,5-dicarboxylic acid diethyl ester

HRID 604450Notes

Reaction equation

HRID 604450 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([O:11][CH2:12][C:13]([F:16])([F:15])[F:14])=[C:9]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[NH:8][N:7]=1)=[O:5])[CH3:2].[H-].[Na+].Br[CH2:25][C:26]([NH:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][N:30]=1)=[O:27]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:10]([O:11][CH2:12][C:13]([F:15])([F:16])[F:14])=[C:9]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:8]([CH2:25][C:26](=[O:27])[NH:28][C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][N:30]=2)[N:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 34211102-Bromo-N-(5-chloro-2-pyridinyl)acetamideHCID 574744254-(2,2,2-Trifluoro-ethoxy)-1H-pyrazole-3,5-dicarboxylic acid diethyl ester

Product 1

HCID 602079691-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-4-(2,2,2-trifluoro-ethoxy)-1H-pyrazole-3,5-dicarboxylic acid diethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 260 mg 4-(2,2,2-Trifluoro-ethoxy)-1H-pyrazole-3,5-dicarboxylic acid diethyl ester in 4 ml absolute DMF 33.5 mg of a 60% suspension of NaH in mineral oil were added under an argon atmosphere. The mixture was stirred for 15 min at RT. Then 209 mg 2-Bromo-N-(5-chloro-pyridin-2-yl)-acetamide were added and the mixture stirred for 2 h at RT. After concentration in vacuo the residue was directly subjected to the next reaction step without further purification.

Workup

  1. stirringthe mixture stirred for 2 h at RT
  2. concentrationAfter concentration in vacuo the residue
  3. customwas directly subjected to the next reaction step without further purification

Sources & evidence

ORD record
ord-ac79d19a92d942edb395e018d1f1ab2f
Source dataset
uspto-grants-2011_03
Patent number
US07910606B2

Reaction notes

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