Reaction #42946

Reaction equation

[6,7-Dimethoxy-4-(4-phenyl-thiazol-2-ylamino)isoquinolin-1-ylmethyl]carbamic acid tert-butyl ester

HCl

→

(1-aminomethyl-6,7-dimethoxy-isoquinolin-4-yl)-(4-phenyl-thiazol-2-yl)amine hydrochloride salt

Yield 71.0%

Solvents

CH2Cl2

dioxane

Conditions

Workup

1. 1
   Filtrationthe suspension was filtered
2. 2
   OtherThe yellow solid was further dried in vacuo

Procedure

[6,7-Dimethoxy-4-(4-phenyl-thiazol-2-ylamino)isoquinolin-1-ylmethyl]carbamic acid tert-butyl ester (44 mg, 0.0853 mmol) in CH2Cl2 (1 mL) was added a 4.0 M HCl solution in dioxane (0.21 mL) at room temp. After the reaction mixture was stirred at room temperature for 21 h, the suspension was filtered. The yellow solid was further dried in vacuo to give (1-aminomethyl-6,7-dimethoxy-isoquinolin-4-yl)-(4-phenyl-thiazol-2-yl)amine hydrochloride salt (26.1 mg; 71%). 1H-NMR (D2O): δ, 8.82 (s, 1H), 7.09-7.00 (m, 6H), 6.69 (s, 1H), 6.51 (s, 1H), 4.43 (s, 2H), 3.70 (s, 3H), 3.59 (s, 3H); MS: calculated for C21H21N4O2S (M−Cl) 393.0; found: 393.0.

Source