Pivaloyl chloride → 5-amino-6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-7-methyl-4H-1-benzopyran-4-one

HRID 1736168Notes

Reaction equation

HRID 1736168 reaction equation
[NH2:1][C:2]1[C:7]2[C:8](=[O:20])[CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([F:19])[CH:13]=3)[O:11][C:6]=2[C:5]([F:21])=[C:4]([CH3:22])[C:3]=1[F:23].[C:24](Cl)(=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26]>N1C=CC=CC=1>[NH2:1][C:2]1[C:7]2[C:8](=[O:20])[CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([NH:18][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])=[C:14]([F:19])[CH:13]=3)[O:11][C:6]=2[C:5]([F:21])=[C:4]([CH3:22])[C:3]=1[F:23]

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 3897105-amino-2-(4-amino-3-fluorophenyl)-6,8-difluoro-7-methyl-4H-1-benzopyran-4-one

Product 1

HCID 194349955-amino-6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-7-methyl-4H-1-benzopyran-4-oneYield 97.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.21 g (3.77 mmol) of Compound 80 obtained in Example 80 (3) was dissolved in 10 mL of pyridine, 0.46 mL (3.77 mmol) of pivaloyl chloride was added under ice-cooling and the mixture was stirred at the same temperature for 1 hour. The reaction solution was poured into ice water and the precipitated crystals were collected by filtration to give 1.48 g of 5-amino-6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-7-methyl-4H-1-benzopyran-4-one (yield: 97%).

Workup

  1. temperaturecooling
  2. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-9c40e017fe1b4660adbd598c8ba2eb02
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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