Water → 2-[4-[N-acetyl-N-(3-azidopropyl)amino]-3-fluorophenyl]-5-amino-6,8-difluoro-4H-1-benzopyran-4-one

HRID 1736150Notes

Reaction equation

[C:1]([N:4]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]3[C:25]([F:26])=[CH:24][C:23]([F:27])=[C:22]([NH2:28])[C:18]=3[C:19](=[O:21])[CH:20]=2)=[CH:11][C:10]=1[F:29])[CH2:5][CH2:6][CH2:7]Cl)(=[O:3])[CH3:2].[N-:30]=[N+:31]=[N-:32].[Na+].O>CN(C)C=O>[C:1]([N:4]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]3[C:25]([F:26])=[CH:24][C:23]([F:27])=[C:22]([NH2:28])[C:18]=3[C:19](=[O:21])[CH:20]=2)=[CH:11][C:10]=1[F:29])[CH2:5][CH2:6][CH2:7][N:30]=[N+:31]=[N-:32])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

810 mg (1.91 mmol) of 2-[4-[N-acetyl-N-(3-chloropropyl)amino]-3-fluorophenyl]-5-amino-6,8-difluoro-4H-1-benzopyran-4-one obtained in Example 50 was dissolved in 40 ml of dimethylformamide under argon atmosphere, 622 mg of sodium azide was added at room temperature and the mixture was stirred at 70° C. for 4 hours. Water was added to the reaction solution, the mixture was extracted twice with ethyl acetate, the organic layer was washed once with water and once with an aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to give 870 mg of 2-[4-[N-acetyl-N-(3-azidopropyl)amino]-3-fluorophenyl]-5-amino-6,8-difluoro-4H-1-benzopyran-4-one.

Workup

extractionthe mixture was extracted twice with ethyl acetate
washthe organic layer was washed once with water and once with an aqueous saturated solution of sodium chloride
dry with materialdried over anhydrous sodium sulfate
distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-946323566bfa4682ba33657cc9df85cb
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05539112

Reaction notes

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