Reaction #42927

Reaction equation

[6,8-dimethoxy-4-(4-methyl-thiazol-2-ylamino)-isoquinolin-1-ylmethyl]carbamic acid tert-butyl ester

HCl

→

(1-aminomethyl-6,8-dimethoxy-isoquinolin-4-yl)-(4-methyl-thiazol-2-yl)amine hydrochloride salt

Yield 53.0%

Solvents

CH2Cl2

dioxane

Conditions

Workup

1. 1
   Filtrationthe resulting yellow solid was collected by suction filtration
2. 2
   Otherdried in vacuo

Procedure

To a solution of [6,8-dimethoxy-4-(4-methyl-thiazol-2-ylamino)-isoquinolin-1-ylmethyl]carbamic acid tert-butyl ester (20 mg, 0.045 mmol) in 1 mL CH2Cl2 was added a 4.0 M HCl solution in dioxane (0.70 mL). After the reaction mixture was stirred at room temperature for 20 h, the resulting yellow solid was collected by suction filtration, and dried in vacuo to give (1-aminomethyl-6,8-dimethoxy-isoquinolin-4-yl)-(4-methyl-thiazol-2-yl)amine hydrochloride salt (9.0 mg, 53%). 1H-NMR (D2O): δ, 8.35 (s, 1H), 6.75 (s, 2H), 6.35 (s, 1H), 4.78 (s, 2H), 3.89 (s, 3H), 3.77 (s, 3H), 2.06 (s, 3H); MS: calculated for C16H19N4O2S (M−Cl) 331.0; found: 331.0.

Source