Reaction #42947

Reaction equation

aluminum

(6,7-dimethoxy-4-thioureido-isoquinolin-1-ylmethyl)carbamic acid tert-butyl ester

chloroacetone

MgSO4

→

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

Solvents

acetone

Conditions

Workup

1. 1
   Otherpreheated to 60° C.
2. 2
   TemperatureThe reaction was cooled
3. 3
   Concentrationconcentrated
4. 4
   OtherThe residue was purified

Procedure

A solution of (6,7-dimethoxy-4-thioureido-isoquinolin-1-ylmethyl)carbamic acid tert-butyl ester (50 mg, 0.127 mmol) and chloroacetone (13.0 mg, 0.140 mmol) in acetone (1.4 mL) in a conical vial was added MgSO4 (7.7 mg, 0.0637 mmol). The resulting suspension was placed in an aluminum block preheated to 60° C. and was allowed to stir for 20 h. The reaction was cooled and concentrated. The residue was purified using a 5 g silica cartridge (MeOH/CH2Cl2, 2:98) to give [6,7-dimethoxy-4-(4-methyl-thiazol-2-ylamino)isoquinolin-1-ylmethyl]carbamic acid tert-butyl ester as a yellow solid (17.4 mg; 32%). MS: calculated for C21H26N4O4S+H 431.0; found: 431.0.

Source