反应 #42925

反应方程式

(4-Amino-6,8-dimethoxy-isoquinolin-1-ylmethyl)carbamic acid tert-butyl ester

benzoylisothiocyanate

→

(6,8-dimethoxy-4-thioureido-isoquinolin-1-ylmethyl)carbamic acid tert-butyl ester

收率 48.0%

溶剂

acetone

反应条件

后处理

1. 1
   浓缩was then concentrated to a yellow solid
2. 2
   其他This solid was triturated with 50% aqueous EtOH
3. 3
   过滤filtered
4. 4
   其他The reaction mixture was placed in an oil bath
5. 5
   温度that was pre-heated to 98° C. for 1 h
6. 6
   workup.DISSOLUTION(the solid was dissolved in 10 min)
7. 7
   温度The mixture was cooled
8. 8
   过滤filtered
9. 9
   洗涤The yellow solid was washed with water
10. 10
    其他dried in vacuo

实验过程

(4-Amino-6,8-dimethoxy-isoquinolin-1-ylmethyl)carbamic acid tert-butyl ester (225 mg, 0.675 mmol) was taken up in 10 mL of dry acetone, and benzoylisothiocyanate (121 mg, 0.742 mmol) was added dropwise. The reaction was stirred at room temperature for 2 h, and was then concentrated to 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, acidified to pH 6-7 by 2.0 N aqueous HCl solution, and filtered. The yellow solid was washed with water, and dried in vacuo to give 126 mg (48%) of (6,8-dimethoxy-4-thioureido-isoquinolin-1-ylmethyl)carbamic acid tert-butyl ester. 1H-NMR (CDCl3): δ, 8.34 (s, 1H), 7.60 (s, 1H), 6.78 (d, 1H, J=2.1 Hz), 6.63 (d, 1H, J=1.9 Hz), 5.06 (d, 2H, J=3.7 Hz), 4.00 (s, 3H), 3.96 (s, 3H), 3.65 (s, 2H), 1.51 (s, 9H); MS: calculated for C18H24N4O4S+H 393.0; found: 393.0.

来源