Dimethylamine → (6-Chloro-3-dimethylaminomethyl-isoquinolin-5-yl)-acetic acid methyl ester

HRID 505213Notes

Reaction equation

HRID 505213 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH2:4][C:5]1[C:14]([Cl:15])=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[C:8]([CH2:16]Br)[N:9]=[CH:10]2.[CH3:19][NH:20][CH3:21]>C1COCC1>[CH3:1][O:2][C:3](=[O:18])[CH2:4][C:5]1[C:14]([Cl:15])=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[C:8]([CH2:16][N:20]([CH3:21])[CH3:19])[N:9]=[CH:10]2

Participants

4

Reactant 2

HCID 674DimethylamineHCID 66880745(3-Bromomethyl-6-chloro-isoquinolin-5-yl)-acetic acid methyl ester

Product 1

HCID 66882460(6-Chloro-3-dimethylaminomethyl-isoquinolin-5-yl)-acetic acid methyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (3-bromomethyl-6-chloro-isoquinolin-5-yl)-acetic acid methyl ester (500 mg, 1.52 mmol) in THF (50 mL) was added a 50% solution of dimethylamine in THF (20 mL). The reaction mixture was stirred for 30 min. at room temperature, followed by removal of the solvents in vacuo. The residue was purified by flash column chromatography (silica gel, gradient of CH2Cl2/MeOH 100:0 to 95:5) to afford the title compound as a yellow oil (445 mg, 1.52 mmol, 100%). MS (ES+): 293 (M(C15H1735ClN2O2)+H)+.

Workup

  1. customfollowed by removal of the solvents in vacuo
  2. customThe residue was purified by flash column chromatography (silica gel, gradient of CH2Cl2/MeOH 100:0 to 95:5)

Sources & evidence

ORD record
ord-c0316fe34d3245cf83f88243293a541d
Source dataset
uspto-grants-2010_08
Patent number
US07781438B2

Reaction notes

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