4-Amino-3,5-dimethylisoxazole → 7-Difluoromethoxy-2-ethylfuro[2,3-c]pyridine-4-carboxylic acid (3,5-dimethylisoxazol-4-yl)amide

HRID 564744Notes

Reaction equation

HRID 564744 reaction equation
[N+](C1C=CC(O[C:11]([C:13]2[C:14]3[CH:25]=[C:24]([CH2:26][CH3:27])[O:23][C:15]=3[C:16]([O:19][CH:20]([F:22])[F:21])=[N:17][CH:18]=2)=[O:12])=CC=1)([O-])=O.[CH3:28][C:29]1[C:33]([NH2:34])=[C:32]([CH3:35])[O:31][N:30]=1>>[CH3:28][C:29]1[C:33]([NH:34][C:11]([C:13]2[C:14]3[CH:25]=[C:24]([CH2:26][CH3:27])[O:23][C:15]=3[C:16]([O:19][CH:20]([F:21])[F:22])=[N:17][CH:18]=2)=[O:12])=[C:32]([CH3:35])[O:31][N:30]=1

Participants

3

Reactant 2

HCID 1820404-Amino-3,5-dimethylisoxazoleHCID 538910297-Difluoromethoxy-2-ethylfuro[2,3-c]pyridine-4-carboxylic acid 4-nitrophenyl ester

Product 1

HCID 536439207-Difluoromethoxy-2-ethylfuro[2,3-c]pyridine-4-carboxylic acid (3,5-dimethylisoxazol-4-yl)amideYield 9.7%

Procedure

This Example was conducted following the procedure of Example 1, but starting from 7-difluoromethoxy-2-ethylfuro[2,3-c]pyridine-4-carboxylic acid 4-nitrophenyl ester (200 mg) and 3,5-dimethylisoxazol-4-ylamine (118 mg). Purification by column chromatography on silica eluting with 30% ethyl acetate in hexane followed by trituration in diethyl ether afforded the title compound as an off-white solid (18 mg).

Workup

  1. customPurification by column chromatography on silica eluting with 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-42b416664123486b978dc326609796b3
Source dataset
uspto-grants-2001_01
Patent number
US06169090A

Reaction notes

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