Tert-Butyl nitrite → N-[2-({1-[1-(4-Fluorophenyl)cyclobutyl]-2-nitroso-1,2,3,4-tetrahydroisoquinolin-7-yl}oxy)ethyl]propane-1-sulfonamide

HRID 242075Notes

Reaction equation

HRID 242075 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH2:23][CH2:24][NH:25][S:26]([CH2:29][CH2:30][CH3:31])(=[O:28])=[O:27])[CH:20]=4)[CH2:15][CH2:14][NH:13]3)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[N:32](OC(C)(C)C)=[O:33]>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH2:23][CH2:24][NH:25][S:26]([CH2:29][CH2:30][CH3:31])(=[O:27])=[O:28])[CH:20]=4)[CH2:15][CH2:14][N:13]3[N:32]=[O:33])[CH2:9][CH2:10][CH2:11]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10906Tert-Butyl nitrite2×HCID 66868509N-[2-({1-[1-(4-Fluorophenyl)cyclobutyl]-1,2,3,4-tetrahydroisoquinolin-7-yl}oxy)ethyl]propane-1-sulfonamide

Product 1

HCID 44465811N-[2-({1-[1-(4-Fluorophenyl)cyclobutyl]-2-nitroso-1,2,3,4-tetrahydroisoquinolin-7-yl}oxy)ethyl]propane-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-[2-({1-[1-(4-Fluorophenyl)cyclobutyl]-1,2,3,4-tetrahydroisoquinolin-7-yl}oxy)ethyl]propane-1-sulfonamide (92 mg, 0.206 mmol, cf. example 65) was dissolved in tetrahydrofuran (1 mL) under an atmosphere of nitrogen. Tert-butyl nitrite (32 mg, 0.309 mmol) were added and the reaction mixture was stirred under reflux for 3 h. After that time additional tert-butyl nitrite (32 mg, 0.309 mmol) was added and stirring under reflux was continued for 2 h. The solvent was evaporated in vacuo and the crude product was purified by flash chromatography (silica, dichloromethane then dichloromethane:methanol=100:1). Yield: 56 mg (0.118 mmol, 57%).

Workup

  1. temperatureunder reflux for 3 h
  2. stirringstirring
  3. temperatureunder reflux
  4. customThe solvent was evaporated in vacuo
  5. customthe crude product was purified by flash chromatography (silica, dichloromethane

Sources & evidence

ORD record
ord-57f17c53992d4928ac8bfe0ff0318c67
Source dataset
uspto-grants-2014_02
Patent number
US08653100B2

Reaction notes

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