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

HRID 1968726Notes

Reaction equation

HRID 1968726 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-f89fd327c2624dc196cf227f07a17ff7
Source dataset
uspto-grants-2013_04
Patent number
US08426440B2

Reaction notes

Loading…