Ethanol → N-(7-isobutylisoquinolin-3-yl)cyclopropanecarboxamide

HRID 468756노트

반응식

HRID 468756 반응식
[CH3:1][C:2]([CH3:20])=[CH:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[C:9]([NH:14][C:15]([CH:17]3[CH2:19][CH2:18]3)=[O:16])[N:10]=[CH:11]2)=[CH:6][CH:5]=1.C(OCC)(=O)C.C(O)C>[Pd]>[CH2:3]([C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[C:9]([NH:14][C:15]([CH:17]3[CH2:19][CH2:18]3)=[O:16])[N:10]=[CH:11]2)=[CH:6][CH:5]=1)[CH:2]([CH3:20])[CH3:1]

참가 물질

5

반응물 3

HCID 702EthanolHCID 8857Ethyl AcetateHCID 67974264N-(7-(2-methylprop-1-enyl)isoquinolin-3-yl)cyclopropanecarboxamide

생성물 1

HCID 67974896N-(7-isobutylisoquinolin-3-yl)cyclopropanecarboxamide수율 70.1%

시약·촉매·용매 1

HCID 23938Palladium촉매2회

실험 절차

To a solution of N-(7-(2-methylprop-1-enyl)isoquinolin-3-yl)cyclopropanecarboxamide (100.0 mg, 0.2891 mmol) in ethyl acetate (10.0 mL, 102 mmol) was added palladium (30.6 mg, 0.0288 mmol) (10 wt % on carbon). The reaction vessel was purged first with nitrogen and then with hydrogen, and stirred at room temperature under a hydrogen balloon for 2 hours. Ethanol (5.0 mL, 86 mmol) and palladium (41.9 mg, 0.0394 mmol) were added, and the reaction maintained at room temperature for 19 hours. The reaction mixture was then filtered through celite and evaporated in vacuo. The crude product was purified via reverse phase HPLC and lyophilized to yield 54.4 mg (70%) of N-(7-isobutylisoquinolin-3-yl)cyclopropanecarboxamide. LCMS (ESI): RT=5.079, M+H=269.1, method=E; 1H NMR (400 MHz, DMSO-d6) δ 10.85 (s, 1H), 9.06 (s, 1H), 8.41 (s, 1H), 7.86-7.70 (m, 2H), 7.54 (dd, J=8.6, 1.3 Hz, 1H), 2.62 (d, J=7.1 Hz, 2H), 2.13-2.01 (m, 1H), 1.94 (dp, J=13.4, 6.7 Hz, 1H), 0.90 (d, J=6.6 Hz, 6H), 0.86-0.75 (m, 4H).

후처리

  1. customThe reaction vessel was purged first with nitrogen
  2. temperaturethe reaction maintained at room temperature for 19 hours
  3. filtrationThe reaction mixture was then filtered through celite
  4. customevaporated in vacuo
  5. customThe crude product was purified via reverse phase HPLC

출처 및 근거

ORD 기록
ord-73b1462aa98446b6aeda1aa3f8fefa33
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623889B2

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