Dichloromethane → 7-(3-hydroxypropylamino)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one

HRID 1162912Notes

Reaction equation

HRID 1162912 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]1[CH:22]=[C:21]2[C:16]([CH:17]=[C:18]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:30]([F:33])([F:32])[F:31])[NH:19][C:20]2=[O:23])=[CH:15][CH:14]=1)(C(C)(C)C)(C)C.C(Cl)Cl>C1COCC1>[OH:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]1[CH:22]=[C:21]2[C:16]([CH:17]=[C:18]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:30]([F:33])([F:31])[F:32])[NH:19][C:20]2=[O:23])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 575581017-[3-(tert-butyldimethylsilyloxy)propylamino]-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one

Product 1

HCID 231567767-(3-hydroxypropylamino)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-oneYield 101.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The 7-[3-(tert-butyldimethylsilyloxy)propylamino]-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (435 mg, 0.913 mmol) obtained in step A was dissolved in THF (9 ml). Thereafter, a 1 M tetrabutylammonium fluoride THF solution (1.1 ml, 1.1 mmol) was added to the obtained solution at a room temperature. The obtained mixture was stirred for 5 hours. Thereafter, methylene chloride was added to the reaction solution. An organic layer thereof was washed with a saturated saline solution, and was then dried over magnesium sulfate, followed by concentration under reduced pressure. The obtained residue was purified by silica gel chromatography (methylene chloride:methanol=30:1), so as to obtain 7-(3-hydroxypropylamino)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (337 mg, 95%).

Workup

  1. washAn organic layer thereof was washed with a saturated saline solution
  2. dry with materialwas then dried over magnesium sulfate
  3. concentrationfollowed by concentration under reduced pressure
  4. customThe obtained residue was purified by silica gel chromatography (methylene chloride:methanol=30:1)

Sources & evidence

ORD record
ord-1fa931e1f50d42229998f1077252e940
Source dataset
uspto-grants-2010_10
Patent number
US07820693B2

Reaction notes

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