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1-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol → HCID 178521389, 화합물

HRID 1777149
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HRID 1777149 반응식
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:18]=[CH:17][CH:16]=[CH:15][C:7]=2[O:8][CH2:9][C:10]([O:12]CC)=O)=[N:2]1.[NH2:19][CH2:20][CH:21]([OH:33])[CH2:22][N:23]1[CH2:32][CH2:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24]1>CCO.C(OCC)(=O)C>[NH:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:18]=[CH:17][CH:16]=[CH:15][C:7]=2[O:8][CH2:9][C:10]([NH:19][CH2:20][CH:21]([OH:33])[CH2:22][N:23]2[CH2:32][CH2:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:24]2)=[O:12])=[N:2]1
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참가 물질

5

반응물 2

HCID 167907201-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-olHCID 178472961HCID 178472961, 화합물

생성물 1

HCID 178521389HCID 178521389, 화합물수율 51%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

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온도
120 °C

실험 절차

To a solution of ethyl 2-(2-(1H-pyrazol-3-yl)phenoxy)acetate (100 mg, 0.41 mmol) in EtOH (10 mL) was added 1-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol (84 mg, 0.41 mmol). The mixture was stirred at 120° C. under microwave heating for 2 h. The reaction mixture was diluted with ethyl acetate (30 mL) and washed with water (10 mL), dried over Na2SO4 and concentrated to give the crude product. The residue was purified by prep-HPLC to afford the desired title compound (85 mg, 44%). 1H NMR (400 MHz, MeOD): δ 7.71-7.69 (m, 2H), 7.34-7.33 (m, 1H), 7.10-7.01 (m, 6H), 6.74 (d, J=2 Hz, 1H), 4.67 (s, 1H), 4.04-4.02 (m, 1H), 3.67 (s, 2H), 3.50-3.49 (m, 1H), 3.37-3.33 (m, 1H), 2.89-2.87 (m, 2H), 2.81-2.78 (m, 2H), 2.58-2.57 (m, 2H) ppm; ESI-MS (m/z): 469.3 [M+1]+.

후처리

  1. temperatureheating for 2 h
  2. washwashed with water (10 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customto give the crude product
  6. customThe residue was purified by prep-HPLC

출처 및 근거

ORD 기록
ord-3dfd0df33ca142b09d703ce802309fca
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09266836B2

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