Methyl iodide → HCID 58246335, compound

HRID 242047Notes

Reaction equation

HRID 242047 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH:13]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH2:24][CH2:25][NH:26][S:27]([CH2:30][CH2:31][CH2:32][CH3:33])(=[O:29])=[O:28])[CH:21]=4)[CH2:16][CH2:15][NH:14]3)[CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[C:34](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O.[OH-].[Na+]>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH:13]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH2:24][CH2:25][NH:26][S:27]([CH2:30][CH2:31][CH2:32][CH3:33])(=[O:28])=[O:29])[CH:21]=4)[CH2:16][CH2:15][N:14]3[CH3:34])[CH2:10][CH2:11][CH2:12]2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 66869440HCID 66869440, compound

Product 1

HCID 58246335HCID 58246335, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 14798Sodium HydroxideSolvent

Procedure

Butane-1-sulfonic acid (2-{1-[1-(4-chloro-phenyl)-cyclobutyl]-1,2,3,4-tetrahydro-isoquinolin-7-yloxy}-ethyl)-amide hydrochloride (example 16, 50.0 mg, 0.10 mmol) is dissolved in acetone (3 ml) and potassium carbonate (29.0 mg, 0.21 mmol) and methyl iodide (16.4 mg, 0.12 mmol) were added. The mixture was stirred at RT for 14 h. The sol-vent was reduced, the reaction mixture was diluted with 1 N sodium hydroxid solution and extracted with dichloromethane. The combined organic layers were washed with saturated sodium chloride solution and dried with potassium sulphate. The residue was purified by HPLC with . . . to give the product (50.0 mg, 0.10 mmol, 13%).

Workup

  1. extractionextracted with dichloromethane
  2. washThe combined organic layers were washed with saturated sodium chloride solution
  3. dry with materialdried with potassium sulphate
  4. customThe residue was purified by HPLC with

Sources & evidence

ORD record
ord-70485b0c8c63422283d5e3c63cd2fffc
Source dataset
uspto-grants-2014_02
Patent number
US08653100B2

Reaction notes

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