1-(1-chloro-6-methoxy-4-phenylisoquinolin-3-yl)-N,N-dimethylmethanamine → 3-[(Dimethylamino)methyl]-6-methoxy-4-phenylisoquinoline-1-carbonitrile

HRID 639877Notes

Reaction equation

HRID 639877 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:4]([CH2:20][N:21]([CH3:23])[CH3:22])[N:3]=1.[C:24]([Cu])#[N:25]>CS(C)=O>[CH3:22][N:21]([CH2:20][C:4]1[N:3]=[C:2]([C:24]#[N:25])[C:11]2[C:6]([C:5]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[CH3:23]

Participants

4

Reactant 2

HCID 117389161-(1-chloro-6-methoxy-4-phenylisoquinolin-3-yl)-N,N-dimethylmethanamineHCID 178418546HCID 178418546, compound

Product 1

HCID 112555843-[(Dimethylamino)methyl]-6-methoxy-4-phenylisoquinoline-1-carbonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 1-(1-chloro-6-methoxy-4-phenylisoquinolin-3-yl)-N,N-dimethylmethanamine (31 mg), 1 mL DMSO, and 16 mg CuCN was stirred at 140 C for 3 h. The solution was cooled and purified directly by reverse-phase HPLC to give the titled compound.

Workup

  1. temperatureThe solution was cooled
  2. custompurified directly by reverse-phase HPLC

Sources & evidence

ORD record
ord-5b91032d9a864e44971efc9f0402ff61
Source dataset
uspto-grants-2010_04
Patent number
US07691879B2

Reaction notes

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