Réaction #42944

Équation de réaction

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

benzoylisothiocyanate

→

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

Rendement 51.0%

Solvants

acetone

Conditions de réaction

Traitement

1. 1
   Concentrationwas concentrated
2. 2
   Autreto yield a yellow solid
3. 3
   AutreThis solid was triturated with 50% aqueous EtOH
4. 4
   Filtrationfiltered
5. 5
   AutreThe reaction mixture was placed in an oil bath
6. 6
   Températurethat was pre-heated to 98° C. for 1 h
7. 7
   workup.DISSOLUTION(the solid was dissolved in 10 min)
8. 8
   TempératureThe mixture was cooled
9. 9
   Filtrationfiltered
10. 10
    LavageThe yellow solid was washed with water
11. 11
    Autredried in vacuo

Mode opératoire

(4-Amino-6,7-dimethoxy-isoquinolin-1-ylmethyl)carbamic acid tert-butyl ester (277 mg, 0.831 mmol) was dissolved in dry acetone, and benzoylisothiocyanate (149 mg, 0.914 mmol) was added dropwise. The reaction was stirred at room temperature for 2 h, and was concentrated to yield a yellow solid. This solid was triturated with 50% aqueous EtOH, filtered, and suspended in 10% NaOH (5.0 mL). The reaction mixture was placed in an oil bath that was pre-heated to 98° C. for 1 h, (the solid was dissolved in 10 min). The mixture was cooled and filtered. The yellow solid was washed with water, and dried in vacuo to give (6,7-dimethoxy-4-thioureido-isoquinolin-1-ylmethyl)carbamic acid tert-butyl ester (165 mg; 51%). 1H-NMR (CDCl3): δ, 8.31 (s, 1H), 7.66 (s, 1H), 7.38 (s, 1H), 4.81 (s, 2H), 4.05 (s, 3H), 4.00 (s, 3H), 2.81 (s, 2H), 1.46 (s, 9H); MS: calculated for C18H24N4O4S+H 393.0; found: 392.9.

Source