4-Benzyloxy-2(1H)-pyridone → 4-Benzyloxy-1-{2-oxo-2-[3-(2,2,2-trifluoro-acetyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]-ethyl}-1H-pyridin-2-one

HRID 564167ノート

反応式

HRID 564167 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.Cl[CH2:17][C:18]([C:20]1[CH:36]=[CH:35][C:23]2[CH2:24][CH2:25][N:26]([C:29](=[O:34])[C:30]([F:33])([F:32])[F:31])[CH2:27][CH2:28][C:22]=2[CH:21]=1)=[O:19]>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:17][C:18](=[O:19])[C:20]2[CH:36]=[CH:35][C:23]3[CH2:24][CH2:25][N:26]([C:29](=[O:34])[C:30]([F:33])([F:31])[F:32])[CH2:27][CH2:28][C:22]=3[CH:21]=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

5

反応物 2

HCID 36077244-Benzyloxy-2(1H)-pyridoneHCID 592398392-chloro-1-[3-(trifluoroacetyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]ethanone

生成物 1

HCID 580428744-Benzyloxy-1-{2-oxo-2-[3-(2,2,2-trifluoro-acetyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]-ethyl}-1H-pyridin-2-one

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To 1.00 g (4.97 mmol) 4-benzyloxy-1H-pyridin-2-one in THF at 0° C. is added subsequently 613 mg (5.47 mmol) potassium-tert-butylate, 92 mg (0.25 mmol) tetra-butylammonium-iodide and 2.38 g (7.46 mmol) 1-[7-(2-chloro-acetyl)-1,2,4,5-tetrahydro-3-benzazepin-3-yl]-2,2,2-trifluoro-ethanone. The reaction mixture is stirred overnight at RT and the solvent is evaporated. The residue is taken up in DCM and aqueous 2M sodium hydroxide solution. The layers are separated, the organic phase is washed with water, dried over MgSO4, filtered and the solvent is evaporated. The residue is purified via chromatography (silica gel; DCM/MeOH 95:5) and then via reverse HPLC purification (Zorbax stable bond, C18; water (0.15% formic acid)/acetonitrile 95:5 to 5:95).

後処理

  1. customthe solvent is evaporated
  2. customThe layers are separated
  3. washthe organic phase is washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent is evaporated
  7. customThe residue is purified via chromatography (silica gel; DCM/MeOH 95:5)
  8. customvia reverse HPLC purification (Zorbax stable bond, C18; water (0.15% formic acid)/acetonitrile 95:5 to 5:95)

出典と根拠

ORDレコード
ord-14014b903b9b4f33a01aa73cab44311e
出典データセット
uspto-grants-2011_11
特許番号
US08067590B2

反応ノート

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