Methylamine → 7-(3-methylaminopropylamino)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one

HRID 1162930Notes

Reaction equation

HRID 1162930 reaction equation
[CH3:1][NH2:2].Br[CH2:4][CH2:5][CH2:6][NH:7][C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[C:13]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]([F:28])([F:27])[F:26])[NH:14][C:15]2=[O:18])=[CH:10][CH:9]=1>>[CH3:1][NH:2][CH2:4][CH2:5][CH2:6][NH:7][C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[C:13]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]([F:28])([F:27])[F:26])[NH:14][C:15]2=[O:18])=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 575581777-(3-bromopropylamino)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one

Product 1

HCID 575581337-(3-methylaminopropylamino)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-oneYield 66%

Procedure

Methylamine (40% methanol solution) was added to the 7-(3-bromopropylamino)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (245 mg, 0.576 mmol) obtained in step A, and the obtained mixture was then stirred at a room temperature for 3 hours. Thereafter, the reaction solvent was distilled away, and the obtained residue was purified by amino silica gel column chromatography (methylene chloride:methanol=20:1), so as to obtain 142 mg of 7-(3-methylaminopropylamino)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (66%).

Workup

  1. distillationThereafter, the reaction solvent was distilled away
  2. customthe obtained residue was purified by amino silica gel column chromatography (methylene chloride:methanol=20:1)

Sources & evidence

ORD record
ord-59db3be2990f4b72a4ee5b9a6c3682ee
Source dataset
uspto-grants-2010_10
Patent number
US07820693B2

Reaction notes

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