반응 #42925

반응 방정식

(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

수율 48.0%

용매

acetone

반응 조건

후처리

1. 1
   농축was then concentrated to a yellow solid
2. 2
   기타This solid was triturated with 50% aqueous EtOH
3. 3
   여과filtered
4. 4
   기타The reaction mixture was placed in an oil bath
5. 5
   온도that was pre-heated to 98° C. for 1 h
6. 6
   workup.DISSOLUTION(the solid was dissolved in 10 min)
7. 7
   온도The mixture was cooled
8. 8
   여과filtered
9. 9
   세척The yellow solid was washed with water
10. 10
    기타dried in vacuo

실험 절차

(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.

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