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

HRID 2186458Notes

Reaction equation

HRID 2186458 reaction equation
[F:1][CH:2]([F:18])[O:3][C:4]1[C:9]2[N:10]=[C:11]([CH2:13][CH3:14])[O:12][C:8]=2[C:7]([C:15]([OH:17])=O)=[CH:6][CH:5]=1.[CH2:19]([N:21]1[C:25]([NH2:26])=[C:24]([CH3:27])[CH:23]=[N:22]1)[CH3:20]>>[CH2:19]([N:21]1[C:25]([NH:26][C:15]([C:7]2[C:8]3[O:12][C:11]([CH2:13][CH3:14])=[N:10][C:9]=3[C:4]([O:3][CH:2]([F:1])[F:18])=[CH:5][CH:6]=2)=[O:17])=[C:24]([CH3:27])[CH:23]=[N:22]1)[CH3:20]

Participants

3

Reactant 2

HCID 224566434-Difluoromethoxy-2-ethylbenzooxazole-7-carboxylic acidHCID 224566581-Ethyl-4-methyl-1H-pyrazol-5-amine

Product 1

HCID 102701224-Difluoromethoxy-2-ethylbenzooxazole-7-carboxylic acid (2-ethyl-4-methyl-2H-pyrazol-3-yl)-amideYield 40%

Procedure

Starting from 4-difluoromethoxy-2-ethylbenzooxazole-7-carboxylic acid (150 mg) and 2-ethyl-4-methyl-2H-pyrazol-3-ylamine (90 mg). Purification by column chromatography on silica eluting 2:1 ethyl acetate-heptane followed by ethyl acetate afforded the title compound as a white solid (85 mg).

Workup

  1. customPurification by column chromatography on silica eluting 2:1 ethyl acetate-heptane

Sources & evidence

ORD record
ord-21921eee26c14d179d3557a468f415d1
Source dataset
uspto-grants-2002_06
Patent number
US06403791B1

Reaction notes

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