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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
ノート
印刷プレビュー

反応式

HRID 1161279 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 962Water
触媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4034bdf3524e46e89b76a9df14542b8e
出典データセット
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07816371B2

反応ノート

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