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

Reaktionsgleichung

Reaktionsgleichung von HRID 564167
[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

Komponenten

5

Edukt 2

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

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-14014b903b9b4f33a01aa73cab44311e
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067590B2

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