Water → HCID 19434889, compound

HRID 1736143Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

177 mg (0.38 mmol) of the resulting 5-(3-chloropropylamino)-6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-4H-1-benzopyran-4-one was dissolved in 10 ml of dimethylformamide under argon atmosphere, 124 mg of sodium azide was added and the mixture was stirred at 70° C. for 18 hours. Water was added to the reaction solution, and the precipitated crystals were collected by filtration and purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1) to give 179 mg (100%) of 5-(3-azidopropylamino)-6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-4H-1-benzopyran-4-one.

Workup

filtrationthe precipitated crystals were collected by filtration
custompurified by silica gel column chromatography (n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record: ord-88fabdc6c2ea48c2b3fbff913aa8ffb5
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05539112

Reaction notes

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