Diethyl Ether → (7R)-7-amino-4-chloro-9-(2,2,2-trifluoroethyl)-6,7,9,10-tetrahydroazepino[3,4-e]indazol-8(3H)-one

HRID 2378913Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2378913
[Cl:1][C:2]1[C:10]2[NH:9][N:8]=[CH:7][C:6]=2[C:5]2[CH2:11][N:12]([CH2:28][C:29]([F:32])([F:31])[F:30])[C:13](=[O:27])[C@H:14]([NH:16]C(=O)OCC3C=CC=CC=3)[CH2:15][C:4]=2[CH:3]=1.C1(OC)C=CC=CC=1.CS(O)(=O)=O.C(OCC)C>ClCCl>[NH2:16][C@H:14]1[C:13](=[O:27])[N:12]([CH2:28][C:29]([F:30])([F:32])[F:31])[CH2:11][C:5]2[C:6]3[CH:7]=[N:8][NH:9][C:10]=3[C:2]([Cl:1])=[CH:3][C:4]=2[CH2:15]1

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 6395Methanesulfonic AcidHCID 7519AnisoleHCID 59732091(R)-Benzyl 4-chloro-8-oxo-9-(2,2,2-trifluoroethyl)-3,6,7,8,9,10-hexahydroazepino[3,4-e]indazol-7-ylcarbamate

Produkt 1

HCID 59732089(7R)-7-amino-4-chloro-9-(2,2,2-trifluoroethyl)-6,7,9,10-tetrahydroazepino[3,4-e]indazol-8(3H)-oneAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(R)-Benzyl 4-chloro-8-oxo-9-(2,2,2-trifluoroethyl)-3,6,7,8,9,10-hexahydroazepino[3,4-e]indazol-7-ylcarbamate (450 mg, 964 μmol) was dissolved in dichloromethane (20 ml). Anisole (250 μl, 2300 μmol) was added to the mixture followed by methanesulfonic acid (5.0 ml, 77051 μmol). Reaction stirred at room temperature for 1.5 hours. 100 mL of diethyl ether was added to the mixture. Reaction stirred at room temperature for 45 minutes. Liquids were decanted off. Remaining solid was washed with diethyl ether and the liquids decanted. Solids were dissolved in water. Mixture was made basic with aqueous sodium bicarbonate. Mixture was extracted twice with ethyl acetate and the aqueous phase was discarded. Material was washed successively with aqueous sodium bicarbonate, water and brine and the aqueous phases were discarded. Organics were dried MgSO4, filtered and then concentrated to dryness. Title compound was obtained as light yellow solid in 78% yield. MS (M+H)−=321.2.

Aufarbeitung

  1. customReaction
  2. customReaction
  3. stirringstirred at room temperature for 45 minutes
  4. customLiquids were decanted off
  5. washRemaining solid was washed with diethyl ether
  6. customthe liquids decanted
  7. dissolutionSolids were dissolved in water
  8. extractionMixture was extracted twice with ethyl acetate
  9. washMaterial was washed successively with aqueous sodium bicarbonate, water and brine
  10. filtrationfiltered
  11. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-b37e0a124d2846c1a8efd552064e64dc
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07470680B2

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