Diethyl Ether → 4-Difluoromethoxy-2-ethylbenzooxazole-7-carboxylic acid (2-methyl-2H-pyrazol-3-yl)-amide

HRID 2186463Notes

Reaction equation

HRID 2186463 reaction equation
[N+](C1C=CC(O[C:11]([C:13]2[C:21]3[O:20][C:19]([CH2:22][CH3:23])=[N:18][C:17]=3[C:16]([O:24][CH:25]([F:27])[F:26])=[CH:15][CH:14]=2)=[O:12])=CC=1)([O-])=O.[CH3:28][N:29]1[C:33]([NH2:34])=[CH:32][CH:31]=[N:30]1.C(OCC)C>CCCCCC>[CH3:28][N:29]1[C:33]([NH:34][C:11]([C:13]2[C:21]3[O:20][C:19]([CH2:22][CH3:23])=[N:18][C:17]=3[C:16]([O:24][CH:25]([F:26])[F:27])=[CH:15][CH:14]=2)=[O:12])=[CH:32][CH:31]=[N:30]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 1369272-Methyl-2H-pyrazol-3-ylamineHCID 545360974-Difluoromethoxy-2-ethylbenzooxazole-7-carboxylic acid 4-nitrophenyl ester

Product 1

HCID 101318274-Difluoromethoxy-2-ethylbenzooxazole-7-carboxylic acid (2-methyl-2H-pyrazol-3-yl)-amideYield 15.7%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Starting from 4-difluoromethoxy-2-ethylbenzooxazole-7-carboxylic acid 4-nitro-phenyl ester (100 mg) and 2-methyl-2H-pyrazole-3-ylamine (51 mg). Purification by column chromatography on silica eluting with ethyl acetate afforded, after trituration with a mixture of diethyl ether and hexane, the title compound as a pale yellow solid (14mg).

Workup

  1. customPurification by column chromatography on silica eluting with ethyl acetate
  2. customafforded

Sources & evidence

ORD record
ord-bcdf2e6c90b44afc930c59b0e6c63fbc
Source dataset
uspto-grants-2002_06
Patent number
US06403791B1

Reaction notes

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