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 564083

Reaktionsgleichung

Reaktionsgleichung von HRID 564083
[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:48]=[CH:47][C:35]2[CH2:36][CH2:37][N:38]([C:41](=[O:46])[C:42]([F:45])([F:44])[F:43])[CH2:39][CH2:40][C:34]=2[CH:33]=1)=[O:31]>C1COCC1.C(OC)(C)(C)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:48]=[CH:47][C:35]3[CH2:36][CH2:37][N:38]([C:41](=[O:46])[C:42]([F:45])([F:43])[F:44])[CH2:39][CH2:40][C:34]=3[CH:33]=2)[C:11](=[O:15])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

8

Edukt 4

HCID 36077244-Benzyloxy-2(1H)-pyridoneHCID 22344722t-Butylammonium IodideHCID 23665647Potassium tert-butoxideHCID 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 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 15413tert-Butyl methyl etherLösungsmittel

Versuchsvorschrift

To 8.05 g (40.0 mmol) 4-benzyloxy-1H-pyridin-2-one in 50 mL THF is added at 0° C. subsequently 4.94 g (44.0 mmol) potassium tert-butylate, 739 mg (2.00 mmol) tert-butyl ammonium-iodide and 15.3 g (48.0 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 poured onto 500 mL water. 100 ml tert-butylmethylether is added. The precipitate is collected and dried. The product, which contains 20% 1-[7-(2-chloro-acetyl)-1,2,4,5-tetrahydro-3-benzazepin-3-yl]-2,2,2-trifluoro-ethanone is used without further purification in the next step.

Aufarbeitung

  1. customThe precipitate is collected
  2. customdried
  3. customis used without further purification in the next step

Quellen und Nachweise

ORD-Eintrag
ord-cf4bd56af3f6478480e28e43ea6cc2eb
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067590B2

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