Methyl iodide → HCID 23156895, compound

HRID 1098299Notes

Reaction equation

HRID 1098299 reaction equation
[CH2:1](N(CC)CC)C.IC.[OH:10][CH:11]1[CH2:16][CH2:15][CH2:14][N:13]([C:17]2[CH:26]=[C:25]3[C:20]([CH:21]=[C:22]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[N:34]4[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]4)[NH:23][C:24]3=[O:27])=[CH:19][CH:18]=2)[CH2:12]1>C(#N)C>[OH:10][CH:11]1[CH2:16][CH2:15][CH2:14][N:13]([C:17]2[CH:26]=[C:25]3[C:20]([CH:21]=[C:22]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[N:34]4[CH2:39][CH2:38][N:37]([CH3:1])[CH2:36][CH2:35]4)[NH:23][C:24]3=[O:27])=[CH:19][CH:18]=2)[CH2:12]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 8471TriethylamineHCID 23156875HCID 23156875, compound

Product 1

HCID 23156895HCID 23156895, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.0185 ml (0.133 mmol) of triethylamine and 0.00665 ml (0.107 mmol) of iodomethane were added to an acetonitrile solution (0.4 ml) containing 3.6 mg (0.0089 mmol) of the 7-(3-hydroxypiperidin-1-yl)-3-(2-piperazin-1-ylphenyl)-2H-isoquinolin-1-one obtained in Example 102. The obtained mixture was stirred at a room temperature for 4 hours. Thereafter, the solvent was distilled away under reduced pressure. The obtained residue was developed and purified by thin-layer chromatography (NH2 F254s, Merck, developing solvent; dichloromethane:methanol=10:1, Rf value: 0.8), so as to obtain 1.8 mg (48%) of 7-(3-hydroxypiperidin-1-yl)-3-[2-(4-methylpiperazin-1-yl)phenyl]-2H-isoquinolin-1-one in the form of a yellow solid.

Workup

  1. distillationThereafter, the solvent was distilled away under reduced pressure
  2. custompurified by thin-layer chromatography (NH2 F254s, Merck, developing solvent; dichloromethane:methanol=10:1, Rf value: 0.8)

Sources & evidence

ORD record
ord-6dd423511a8e48a6a2723c1faec61b98
Source dataset
uspto-grants-2012_03
Patent number
US08143274B2

Reaction notes

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