Potassium Carbonate → HCID 66857697, Verbindung

HRID 2037542Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2037542
CS(O[CH2:6][CH2:7][C@@:8]1([C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)[O:13][C:12](=[O:14])[N:11]([C@H:15]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=3[F:30])=[CH:19][CH:18]=2)[CH3:16])[CH2:10][CH2:9]1)(=O)=O.[NH:38]1[CH:42]=[CH:41][N:40]=[C:39]1[NH2:43].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[NH:38]1[CH:42]=[CH:41][N:40]=[C:39]1[NH:43][CH2:6][CH2:7][C@@:8]1([C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)[O:13][C:12](=[O:14])[N:11]([C@H:15]([C:17]2[CH:18]=[CH:19][C:20]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=3[F:30])=[CH:21][CH:22]=2)[CH3:16])[CH2:10][CH2:9]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 821402-AminoimidazoleHCID 86649947HCID 86649947, Verbindung

Produkt 1

HCID 66857697HCID 66857697, VerbindungAusbeute 19,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 2-((S)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)ethyl methanesulfonate (40 mg, 0.07 mmol), 1H-imidazol-2-amine (18 mg, 0.21 mmol), K2CO3 (29 mg, 0.21 mmol) in acetonitrile (4 mL) was heated to reflux overnight. The solvent was removed and the residue was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc and the combined organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to give the crude product. It was purified by preparative HPLC to give (R)-6-(2-(1H-imidazol-2-ylamino)ethyl)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one (7 mg, 17%). LC-MS Method 3 tR=1.15, min, m/z=521; 1H NMR (CDCl3): 1.55 (m, 3H), 2.16-2.33 (m, 7H), 2.94 (m, 1H), 3.56 (m, 1H), 4.02 (m, 1H), 5.66 (m, 1H), 6.25 (m, 1H), 6.52 (m, 1H), 6.90 (m, 2H), 7.04 (m, 4H), 7.18 (m, 2H), 7.26 (m, 3H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customThe solvent was removed
  4. customthe residue was partitioned between EtOAc and water
  5. extractionThe aqueous layer was extracted with EtOAc
  6. washthe combined organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give the crude product
  11. customIt was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-e4e4a268dae14959967c9da889e167b4
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575156B2

Notizen zur Reaktion

Wird geladen…