Water → N-acetyl-N-(4-bromoisoquinolin-1-yl)acetamide

HRID 1922905노트

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HRID 1922905 반응식
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH2:12])=[N:4][CH:3]=1.C(N([CH2:20][CH3:21])C(C)C)(C)C.[C:22](Cl)(=[O:24])[CH3:23].[OH2:26]>C(Cl)Cl>[C:22]([N:12]([C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([Br:1])=[CH:3][N:4]=1)[C:20](=[O:26])[CH3:21])(=[O:24])[CH3:23]

참가 물질

6

반응물 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 3118704-Bromo-1-isoquinolinamine

생성물 1

HCID 59605275N-acetyl-N-(4-bromoisoquinolin-1-yl)acetamide수율 85%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

To a solution of 4-bromoisoquinolin-1-amine (403 mg, 1.81 mmol) in methylene chloride (11 mL) at 0° C. was added N,N-diisopropylethylamine (1.57 mL, 9.03 mmol), followed by acetyl chloride (0.321 mL, 4.52 mmol) dropwise. The mixture was stirred at 0° C. for 10 min then at room temperature for 2 h. The mixture was diluted with DCM (10 mL). Water (20 mL) was added. The organic layer was separated. The aqueous solution was extracted with DCM (10 mL). The combined DCM solutions were dried (Na2SO4). After filtration and concentration, the crude was purified with flash chromatography to give the desired product (470 mg, 85%). 1H NMR (400 MHz, DMSO) δ 8.79 (s, 1H), 8.23 (d, J=8.4, 1H), 8.13 (d, J=8.4, 1H), 8.05 (t, J=7.7, 1H), 7.87 (t, J=7.6, 1H), 2.23 (s, 6H).

후처리

  1. waitat room temperature for 2 h
  2. customThe organic layer was separated
  3. extractionThe aqueous solution was extracted with DCM (10 mL)
  4. dry with materialThe combined DCM solutions were dried (Na2SO4)
  5. filtrationAfter filtration and concentration
  6. customthe crude was purified with flash chromatography

출처 및 근거

ORD 기록
ord-5b0d66967ad04c65bd82509cfc9a1a0e
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173650B2

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