HCID 19434931, compound → HCID 19434996, compound
Reaction equation
[NH2:1][C:2]1[C:7]([Br:8])=[CH:6][C:5]([C:9]2[O:10][C:11]3[C:19]([F:20])=[CH:18][C:17]([F:21])=[C:16]([NH:22]C(=O)C(C)(C)C)[C:12]=3[C:13](=[O:15])[CH:14]=2)=[CH:4][C:3]=1[Br:29]>S(=O)(=O)(O)O>[NH2:22][C:16]1[C:12]2[C:13](=[O:15])[CH:14]=[C:9]([C:5]3[CH:6]=[C:7]([Br:8])[C:2]([NH2:1])=[C:3]([Br:29])[CH:4]=3)[O:10][C:11]=2[C:19]([F:20])=[CH:18][C:17]=1[F:21]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
20 ml of concentrated sulfuric acid was added to the resulting 1.00 g (1.89 mmol) of 2-(4-amino-3,5-dibromophenyl)-6,8-difluoro-5-pivaloylamino-4H-1-benzopyran-4-one and the mixture was stirred at 100° C. for 1.3 hours. The reaction solution was adjusted to pH 9 by addition of ice and a 10N aqueous solution of sodium hydroxide thereto and the precipitated crystals were collected by filtration. The crystals were purified by silica gel column chromatography (chloroform:acetonitrile=40:1) and triturated with chloroform to give 378 mg (45%) of Compound 36.
Workup
- additionThe reaction solution was adjusted to pH 9 by addition of ice
- filtrationa 10N aqueous solution of sodium hydroxide thereto and the precipitated crystals were collected by filtration
- customThe crystals were purified by silica gel column chromatography (chloroform:acetonitrile=40:1)
- customtriturated with chloroform
Sources & evidence
- ORD record
- ord-c2851698e37849f99a2fdf5a82f6c66a
- Source dataset
- uspto-grants-1996_07
- Patent number
- US05539112
Reaction notes
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