4-Benzyloxy-2(1H)-pyridone → 4-Benzyloxy-1-{2-oxo-2-[2-(2,2,2-trifluoro-acetyl)-1,2,3,4-tetrahydro-isoquinolin-7-yl]-ethyl}-1H-pyridin-2-one

HRID 564202

反応式

HRID 564202 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][NH:12][C:11](=[O:15])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC([O-])(C)C.[K+].[I-].C([NH3+])(C)(C)C.Cl[CH2:29][C:30]([C:32]1[CH:41]=[C:40]2[C:35]([CH2:36][CH2:37][N:38]([C:42](=[O:47])[C:43]([F:46])([F:45])[F:44])[CH2:39]2)=[CH:34][CH:33]=1)=[O:31]>C1COCC1.CCOC(C)=O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:29][C:30](=[O:31])[C:32]2[CH:41]=[C:40]3[C:35]([CH2:36][CH2:37][N:38]([C:42](=[O:47])[C:43]([F:46])([F:44])[F:45])[CH2:39]3)=[CH:34][CH:33]=2)[C:11](=[O:15])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 36077244-Benzyloxy-2(1H)-pyridoneHCID 22344722t-Butylammonium IodideHCID 23665647Potassium tert-butoxideHCID 866236881-[7-(2-chloro-acetyl)-3,4-dihydro-1H-isoquinolin-2-yl]-2,2,2-trifluoro-ethanone2 回

生成物 1

HCID 441936264-Benzyloxy-1-{2-oxo-2-[2-(2,2,2-trifluoro-acetyl)-1,2,3,4-tetrahydro-isoquinolin-7-yl]-ethyl}-1H-pyridin-2-one

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To 600 mg (2.98 mmol) 4-benzyloxy-1H-pyridin-2-one in 6 mL THF is added at 0° C. 368 mg (3.28 mmol) potassium tert-butylate and 55 mg (0.15 mmol) tert-butylammonium iodide. After 5 min 1.00 g (3.28 mmol) 1-[7-(2-chloro-acetyl)-3,4-dihydro-1H-isoquinolin-2-yl]-2,2,2-trifluoro-ethanone is added. After 2 h additional 600 mg (1.97 mmol) 1-[7-(2-chloro-acetyl)-3,4-dihydro-1H-isoquinolin-2-yl]-2,2,2-trifluoro-ethanone is added and the mixture is stirred an additional hour. The reaction mixture is diluted with EtOAc and the organic phase is washed with water, filtered, dried over MgSO4 and the solvent is evaporated. The residue is purified via reverse HPLC chromatography (Zorbax stable bond; water (0.15% formic acid)/acetonitrile (0.15% formic acid) 95:5 to 5:95).

後処理

  1. washthe organic phase is washed with water
  2. filtrationfiltered
  3. dry with materialdried over MgSO4
  4. customthe solvent is evaporated
  5. customThe residue is purified via reverse HPLC chromatography (Zorbax stable bond; water (0.15% formic acid)/acetonitrile (0.15% formic acid) 95:5 to 5:95)

出典と根拠

ORDレコード
ord-769f935b5fc048af99b9866c309dba05
出典データセット
uspto-grants-2011_11
特許番号
US08067590B2

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