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Methanol → (R)-N-(6-Chloro-2-(1-hydroxypropan-2-yl)-1-oxo-1,2-dihydroisoquinolin-5-yl)-2-(3-fluoro-4-(trifluoromethyl)phenyl)acetamide

HRID 1161279
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HRID 1161279 반응식
C([O:4][CH2:5][C@H:6]([N:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Cl:33])[C:14]=2[NH:18][C:19](=[O:32])[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[C:23]([F:31])[CH:22]=2)[C:9]1=[O:34])[CH3:7])(=O)C.C(=O)([O-])[O-].[K+].[K+].CO>O>[Cl:33][C:13]1[C:14]([NH:18][C:19](=[O:32])[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:28])[F:29])=[C:23]([F:31])[CH:22]=2)=[C:15]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:34])[N:8]([C@H:6]([CH3:7])[CH2:5][OH:4])[CH:17]=[CH:16]2
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참가 물질

5

반응물 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 59515861(R)-2-(6-Chloro-5-(2-(3-fluoro-4-(trifluoromethyl)phenyl)acetamido)-1-oxoisoquinolin-2(1H)-yl)propyl acetate

생성물 1

HCID 25013762(R)-N-(6-Chloro-2-(1-hydroxypropan-2-yl)-1-oxo-1,2-dihydroisoquinolin-5-yl)-2-(3-fluoro-4-(trifluoromethyl)phenyl)acetamide

시약·촉매·용매 1

HCID 962
Water
촉매

실험 절차

A round bottom flask was charged with (R)-2-(6-chloro-5-(2-(3-fluoro-4-(trifluoromethyl)phenyl)acetamido)-1-oxoisoquinolin-2(1H)-yl)propyl acetate (1.200 g, 0.002406 mol), potassium carbonate (0.997 g, 0.00722 mol) and methanol (20 mL, 0.5 mol) and 2 drops of water. The reaction was stirred at room temperature for 1 hour in which time the reaction was complete. The reaction mixture was filtered over Na2SO4 and washed repeatedly with methanol. The solvent was removed under reduced pressure and the residue purified by flash chromatography to obtain the product as a white solid. MS m/z=457.3 (M+H). 1H NMR (400 MHz, DMSO-d6): δ 10.20 (s, 1H), 8.17 (d, J=8.54 Hz, 1H), 7.79 (t, J=8.21 Hz, 1H), 7.60 (d, J=8.87 Hz, 1H), 7.56-7.51 (m, 2H), 7.45 (d, J=8.54 Hz, 1H), 6.44 (d, J=7.90 Hz, 1H), 5.03-4.99 (m, 1H), 4.94 (t, J=5.21 Hz, 1H), 3.94 (s, 2H), 3.68-3.56 (m, 2H), 1.28 (d, J=7.51 Hz, 3H).

후처리

  1. filtrationThe reaction mixture was filtered over Na2SO4
  2. washwashed repeatedly with methanol
  3. customThe solvent was removed under reduced pressure
  4. customthe residue purified by flash chromatography

출처 및 근거

ORD 기록
ord-4034bdf3524e46e89b76a9df14542b8e
출처 데이터셋
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07816371B2

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