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

HRID 33250

Reaction equation

HRID 33250 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:8][N:7]=1)=[O:5])[CH3:2].[H-].[Na+].Br[CH2:19][C:20]([NH:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][N:24]=1)=[O:21]>CN(C=O)C>[CH2:14]([O:13][C:11]([C:9]1[CH:10]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[N:7]([CH2:19][C:20](=[O:21])[NH:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][N:24]=2)[N:8]=1)=[O:12])[CH3:15]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 142184diethyl 1H-pyrazole-3,5-dicarboxylateHCID 34211102-Bromo-N-(5-chloro-2-pyridinyl)acetamide

Product 1

HCID 602079571-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-1H-pyrazole-3,5-dicarboxylic acid diethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 10 g 1H-Pyrazole-3,5-dicarboxylic acid diethyl ester in 200 ml absolute DMF 1.885 g of a 60% suspension of NaH in mineral oil were added in an argon atmosphere. The mixture was stirred for 15 min at RT. 11.76 g 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 purified by chromatography on silica gel using CH2Cl2/ethylacetate=8/2. The fractions containing the product were evaporated. Yield: 16.05 g.

Workup

  1. stirringthe mixture stirred for 2 h at RT
  2. concentrationAfter concentration in vacuo the residue
  3. customwas purified by chromatography on silica gel
  4. additionThe fractions containing the product
  5. customwere evaporated

Sources & evidence

ORD record
ord-e88c35d032e04b21ac5ba4ec27b8a34a
Source dataset
uspto-grants-2008_09
Patent number
US07429581B2

Linked notes

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