Benzoyl isothiocyanate → (6,7-Dimethoxy-4-thioureido-isoquinolin-1-ylmethyl)carbamic acid tert-butyl ester

HRID 14666

반응식

HRID 14666 반응식
[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=2)[C:12]([NH2:23])=[CH:11][N:10]=1)([CH3:4])([CH3:3])[CH3:2].C([N:33]=[C:34]=[S:35])(=O)C1C=CC=CC=1>CC(C)=O>[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=2)[C:12]([NH:23][C:34]([NH2:33])=[S:35])=[CH:11][N:10]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

4

반응물 2

HCID 68284Benzoyl isothiocyanateHCID 59341104(4-Amino-6,7-dimethoxy-isoquinolin-1-ylmethyl)carbamic acid tert-butyl ester

생성물 1

HCID 59341094(6,7-Dimethoxy-4-thioureido-isoquinolin-1-ylmethyl)carbamic acid tert-butyl ester수율 51%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

(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.

후처리

  1. concentrationwas concentrated
  2. customto yield a yellow solid
  3. customThis solid was triturated with 50% aqueous EtOH
  4. filtrationfiltered
  5. customThe reaction mixture was placed in an oil bath
  6. temperaturethat was pre-heated to 98° C. for 1 h
  7. dissolution(the solid was dissolved in 10 min)
  8. temperatureThe mixture was cooled
  9. filtrationfiltered
  10. washThe yellow solid was washed with water
  11. customdried in vacuo

출처 및 근거

ORD 기록
ord-e7ffdc103642418580c6f93f4adce9fd
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732446B1

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