Dimethylamine, hydrochloride → 5-(5-dimethylaminopentylamino)-6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-4H-1-benzopyran-4-one

HRID 1736218Notes

Reaction equation

HRID 1736218 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]1[C:13]2[C:14](=[O:32])[CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])=[C:20]([F:31])[CH:19]=3)[O:17][C:12]=2[C:11]([F:33])=[CH:10][C:9]=1[F:34].Cl.[CH3:36][NH:37][CH3:38].C(=O)([O-])[O-].[K+].[K+]>>[CH3:36][N:37]([CH3:38])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]1[C:13]2[C:14](=[O:32])[CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])=[C:20]([F:31])[CH:19]=3)[O:17][C:12]=2[C:11]([F:33])=[CH:10][C:9]=1[F:34]

Participants

4

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 194348655-(5-bromopentylamino)-6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-4H-1-benzopyran-4-one

Product 1

HCID 194348925-(5-dimethylaminopentylamino)-6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-4H-1-benzopyran-4-oneYield 74%

Procedure

Substantially the same manner as that in Example 130 (1) was repeated except that 1.47 g (2.73 mmol) of the above 5-(5-bromopentylamino)-6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-4H-1-benzopyran-4-one was reacted with 2.22 g (27.3 mmol) of dimethylamine hydrochloride and 3.77 g (27.3 mmol) of potassium carbonate and the resulting compound was purified by silica gel column chromatography (chloroform:methanol=9:1), to give 1.02 g. of 5-(5-dimethylaminopentylamino)-6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-4H-1-benzopyran-4-one (yield: 74%).

Workup

  1. customthe resulting compound was purified by silica gel column chromatography (chloroform:methanol=9:1)
  2. customto give 1.02 g

Sources & evidence

ORD record
ord-10e8de94c6a64a91b65037befbeecdd7
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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