4-Bromo-1-methyl-1H-pyrazol-5-amine → 4-Difluoromethoxy-2-ethylbenzooxazole-7-carboxylic acid (4-bromo-2-methyl-2H-pyrazol-3-yl)-amide

HRID 2186462Notes

Reaction equation

HRID 2186462 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.[Br:28][C:29]1[CH:33]=[N:32][N:31]([CH3:34])[C:30]=1[NH2:35]>C(OCC)C>[Br:28][C:29]1[CH:33]=[N:32][N:31]([CH3:34])[C:30]=1[NH:35][C:11]([C:13]1[C:21]2[O:20][C:19]([CH2:22][CH3:23])=[N:18][C:17]=2[C:16]([O:24][CH:25]([F:26])[F:27])=[CH:15][CH:14]=1)=[O:12]

Participants

4

Reactant 2

HCID 6003514-Bromo-1-methyl-1H-pyrazol-5-amineHCID 545360974-Difluoromethoxy-2-ethylbenzooxazole-7-carboxylic acid 4-nitrophenyl ester

Product 1

HCID 102732694-Difluoromethoxy-2-ethylbenzooxazole-7-carboxylic acid (4-bromo-2-methyl-2H-pyrazol-3-yl)-amideYield 6.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Starting from 4-difluoromethoxy-2-ethylbenzooxazole-7-carboxylic acid 4-nitro-phenyl ester (100 mg) and 4-bromo-2-methyl-2H-pyrazol-3-ylamine (93 mg). Purification by column chromatography on silica eluting with 1-5% methanol in dichloromethane afforded, after trituration with diethyl ether, the title compound as a white solid (7 mg).

Workup

  1. customPurification by column chromatography on silica eluting with 1-5% methanol in dichloromethane
  2. customafforded

Sources & evidence

ORD record
ord-f37cfa70122e455ca0c51294c7801dd5
Source dataset
uspto-grants-2002_06
Patent number
US06403791B1

Reaction notes

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