Cyanuric chloride → 7-Difluoromethoxy-2-methoxymethylbenzofuran-4-carboxylic acid (3,5-dimethylisoxazol-4-yl)-amide

HRID 1282045Notes

Reaction equation

HRID 1282045 reaction equation
N1C(Cl)=NC(Cl)=NC=1Cl.C(N(CC)CC)C.[F:17][CH:18]([F:35])[O:19][C:20]1[CH:21]=[CH:22][C:23]([C:32]([OH:34])=O)=[C:24]2[C:28]=1[O:27][C:26]([CH2:29][O:30][CH3:31])=[CH:25]2.[CH3:36][C:37]1[C:41]([NH2:42])=[C:40]([CH3:43])[O:39][N:38]=1>ClCCl>[CH3:36][C:37]1[C:41]([NH:42][C:32]([C:23]2[CH:22]=[CH:21][C:20]([O:19][CH:18]([F:17])[F:35])=[C:28]3[O:27][C:26]([CH2:29][O:30][CH3:31])=[CH:25][C:24]=23)=[O:34])=[C:40]([CH3:43])[O:39][N:38]=1

Participants

6

Reactant 4

HCID 7954Cyanuric chlorideHCID 8471TriethylamineHCID 1820404-Amino-3,5-dimethylisoxazoleHCID 184236437-Difluoromethoxy-2-methoxymethylbenzofuran-4-carboxylic acid

Product 1

HCID 101334777-Difluoromethoxy-2-methoxymethylbenzofuran-4-carboxylic acid (3,5-dimethylisoxazol-4-yl)-amideYield 28.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cyanuric chloride (19 mg) and triethylamine (0.05 ml) were added to a stirred solution of 7-difluoromethoxy-2-methoxymethylbenzofuran-4-carboxylic acid (85 mg) in dry dichloromethane at room temperature under a dry nitrogen atmosphere. After stirring for 20 minutes 3,5-dimethylisoxazol-4-ylamine (42 mg) was added and the reaction left overnight. The reaction was mixture was preadsorbed onto silica. Purification by column chromatography on silica eluting with 30% ethyl acetate in hexane gave the title compound as a cream solid (33 mg)

Workup

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

Sources & evidence

ORD record
ord-de8416fb1cb1469799b77a1ea970b8a3
Source dataset
uspto-grants-2002_09
Patent number
US06455561B1

Reaction notes

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