1-Propanesulfonyl chloride → HCID 86653006, compound

HRID 242104Notes

Reaction equation

HRID 242104 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([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:5]=[CH:4][CH:3]=1.[CH2:26]([S:29](Cl)(=[O:31])=[O:30])[CH2:27][CH3:28]>N1C=CC=CC=1>[Cl:1][C:2]1[N:7]=[C:6]([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:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 662791-Propanesulfonyl chlorideHCID 58246282HCID 58246282, compound

Product 1

HCID 86653006HCID 86653006, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-({1-[1-(6-Chloropyridin-2-yl)cyclobutyl]-3,4-dihydroisoquinolin-7-yl}oxy)ethanamine (80 mg, 0.225 mmol) was dissolved in pyridine and propane-1-sulfonyl chloride (29 μl, 0.25 mmol) were added. The reaction mixture was stirred at room temperature over night. The solvent was evaporated in vacuo. Toluene was added to the residue and the solvent was evaporated in vacuo (repeated twice). The crude product was purified by flash chromatography (silica, dichloromethane, methanol). Yield: 36 mg (0.078 mmol, 35%).

Workup

  1. customThe solvent was evaporated in vacuo
  2. additionToluene was added to the residue
  3. customthe solvent was evaporated in vacuo (
  4. customThe crude product was purified by flash chromatography (silica, dichloromethane, methanol)

Sources & evidence

ORD record
ord-63954aeb78634383bb72650a6d9b1eb5
Source dataset
uspto-grants-2014_02
Patent number
US08653100B2

Reaction notes

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