Water → 5-(4-azidobutylamino)-6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-4H-1-benzopyran-4-one

HRID 1736209Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]1[C:12]2[C:13](=[O:31])[CH:14]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])=[C:19]([F:30])[CH:18]=3)[O:16][C:11]=2[C:10]([F:32])=[CH:9][C:8]=1[F:33].[N-:34]=[N+:35]=[N-:36].[Na+].O>CN(C)C=O>[N:34]([CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]1[C:12]2[C:13](=[O:31])[CH:14]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])=[C:19]([F:30])[CH:18]=3)[O:16][C:11]=2[C:10]([F:32])=[CH:9][C:8]=1[F:33])=[N+:35]=[N-:36]

Participants

Conditions

Temperature: 70 °C

Procedure

489 mg (1.02 mmol) of the above 5-(4-chlorobutylamino)-6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-4H-1-benzopyran-4-one was dissolved in 20 mL of dimethylformamide under argon atmosphere, 332 mg (5.10 mmol) of sodium azide was added and the mixture was stirred at 70° C. for 10 hours. Water was added to the reaction solution and the precipitated crystals were collected by filtration to give 332 mg of 5-(4-azidobutylamino)-6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-4H-1-benzopyran-4-one (yield: 67%).

Workup

filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record: ord-031621e1bc0449b69cf083768b248617
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05539112

Reaction notes

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