5-Amino-1-methyl-1H-pyrazole-4-carbonitrile → 4-Difluoromethoxy-2-ethylbenzooxazole-7-carboxylic acid (4-cyano-2-methyl-2H-pyrazol-3-yl)-amide

HRID 2186461Notes

Reaction equation

HRID 2186461 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[NH2:11][C:12]1[N:16]([CH3:17])[N:15]=[CH:14][C:13]=1[C:18]#[N:19].[N+](C1C=CC([O:29][C:30]([C:32]2[C:40]3[O:39][C:38]([CH2:41][CH3:42])=[N:37][C:36]=3[C:35]([O:43][CH:44]([F:46])[F:45])=[CH:34][CH:33]=2)=O)=CC=1)([O-])=O>CN(C)C=O>[C:18]([C:13]1[CH:14]=[N:15][N:16]([CH3:17])[C:12]=1[NH:11][C:30]([C:32]1[C:40]2[O:39][C:38]([CH2:41][CH3:42])=[N:37][C:36]=2[C:35]([O:43][CH:44]([F:45])[F:46])=[CH:34][CH:33]=1)=[O:29])#[N:19]

Participants

5

Reactant 3

HCID 2197405-Amino-1-methyl-1H-pyrazole-4-carbonitrileHCID 2724254Sodium bis(trimethylsilyl)amideHCID 545360974-Difluoromethoxy-2-ethylbenzooxazole-7-carboxylic acid 4-nitrophenyl ester

Product 1

HCID 101331814-Difluoromethoxy-2-ethylbenzooxazole-7-carboxylic acid (4-cyano-2-methyl-2H-pyrazol-3-yl)-amideYield 26.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium bis(trimethylsilyl)amide (0.53 ml) was added to a solution of 5-amino-1-methyl-1H-pyrazole-4-carbonitrile (65 mg) in N,N-dimethylformamide (5 ml) at room temperature under an atmosphere of nitrogen. The mixture was stirred for 10 minutes before addition of 4-difluoromethoxy-2-ethylbenzooxazole-7-carboxylic acid 4-nitrophenyl ester (100 mg), then for 90 minutes. It was quenched with water (1 ml) and the solvent removed in vacuo. Purification by column chromatography on silica eluting with 2:1 heptane-ethyl acetate afforded the title compound as a white solid (25 mg).

Workup

  1. customIt was quenched with water (1 ml)
  2. customthe solvent removed in vacuo
  3. customPurification by column chromatography on silica eluting with 2:1 heptane-ethyl acetate

Sources & evidence

ORD record
ord-3f5688cfbf6a43cca8a063415486ce00
Source dataset
uspto-grants-2002_06
Patent number
US06403791B1

Reaction notes

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