1-Propanesulfonyl chloride → N-[2-({1-[1-(4-Fluorophenyl)cyclobutyl]-3,4-dihydroisoquinolin-7-yl}oxy)ethyl]propane-1-sulfonamide

HRID 242061Notes

Reaction equation

HRID 242061 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH2:23][CH2:24][NH2:25])[CH:20]=4)[CH2:15][CH2:14][N:13]=3)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH2:26]([S:29](Cl)(=[O:31])=[O:30])[CH2:27][CH3:28]>ClCCl.CN(C)C1C=CN=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH2:23][CH2:24][NH:25][S:29]([CH2:26][CH2:27][CH3:28])(=[O:31])=[O:30])[CH:20]=4)[CH2:15][CH2:14][N:13]=3)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 662791-Propanesulfonyl chlorideHCID 582463242-({1-[1-(4-Fluorophenyl)cyclobutyl]-3,4-dihydroisoquinolin-7-yl}oxy)ethanamine

Product 1

HCID 66868742N-[2-({1-[1-(4-Fluorophenyl)cyclobutyl]-3,4-dihydroisoquinolin-7-yl}oxy)ethyl]propane-1-sulfonamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent3×

Procedure

2-({1-[1-(4-Fluorophenyl)cyclobutyl]-3,4-dihydroisoquinolin-7-yl}oxy)ethanamine (298 mg, 0.88 mmol) was dissolved in dichloromethane (10 mL) and N,N-dimethylpyridin-4-amine (118 mg, 0.97 mmol) was added. After dropwise addition of a solution of propane-1-sulfonyl chloride (138 mg, 0.97 mmol) in dichloromethane (2 mL) stirring was continued over night. The reaction mixture was diluted with dichloromethane (20 mL), washed with an aqueous ammonium chloride solution (30 mL). The organic layer was dried (MgSO4) and concentrated in vacuo. The crude product was purified by flash chromatography (silica, ethyl acetate:dichloromethane=1:10). Yield: 200 mg (0.45 mmol, 51%).

Workup

  1. waitwas continued over night
  2. washwashed with an aqueous ammonium chloride solution (30 mL)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash chromatography (silica, ethyl acetate:dichloromethane=1:10)

Sources & evidence

ORD record
ord-70d3b8c1787249b8ba4ed5ff4155a02e
Source dataset
uspto-grants-2014_02
Patent number
US08653100B2

Reaction notes

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