Acetic Acid → (R)-4-chloro-8-oxo-9-(2,2,2-trifluoroethyl)-3,6,7,8,9,10-hexahydroazepino[3,4-e]indazol-7-yl benzoate

HRID 2378910Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2378910
[C:1]([O:9][C@H:10]([CH2:15][C:16]1[C:17]([CH2:26][NH:27][CH2:28][C:29]([F:32])([F:31])[F:30])=[C:18]2[C:22](=[C:23]([Cl:25])[CH:24]=1)[NH:21][N:20]=[CH:19]2)[C:11]([O:13]C)=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.C(O)(=O)C>>[C:1]([O:9][C@H:10]1[C:11](=[O:13])[N:27]([CH2:28][C:29]([F:31])([F:32])[F:30])[CH2:26][C:17]2[C:18]3[CH:19]=[N:20][NH:21][C:22]=3[C:23]([Cl:25])=[CH:24][C:16]=2[CH2:15]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 3

HCID 176Acetic AcidHCID 1140TolueneHCID 59732084(R)-3-(7-chloro-4-((2,2,2-trifluoroethylamino)methyl)-1H-indazol-5-yl)-1-methoxy-1-oxopropan-2-yl benzoate

Produkt 1

HCID 59732073(R)-4-chloro-8-oxo-9-(2,2,2-trifluoroethyl)-3,6,7,8,9,10-hexahydroazepino[3,4-e]indazol-7-yl benzoateAusbeute 74 %

Versuchsvorschrift

(R)-3-(7-chloro-4-((2,2,2-trifluoroethylamino)methyl)-1H-indazol-5-yl)-1-methoxy-1-oxopropan-2-yl benzoate (7.75 g, 16.5 mmol) in toluene (70.00 ml, 657 mmol) was added acetic acid (1.2 ml, 20.96 mmol) and refluxed for 12 h. The solvent was evaporated and the crude product was dissolved in EtOAc, washed with aqueous NaHCO3. The solvent was removed and the crude product was purified by flash chromatography using 50% EtOAc in hexane to give (R)-4-chloro-8-oxo-9-(2,2,2-trifluoroethyl)-3,6,7,8,9,10-hexahydroazepino[3,4-e]indazol-7-yl benzoate in 74% yield. MS (ESI) 438 (M+H); Rf=2.60.

Aufarbeitung

  1. temperaturerefluxed for 12 h
  2. customThe solvent was evaporated
  3. dissolutionthe crude product was dissolved in EtOAc
  4. washwashed with aqueous NaHCO3
  5. customThe solvent was removed
  6. customthe crude product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b797a760dc294f55afe8aa4699dd394d
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07470680B2

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