Potassium Carbonate → 5-(3,4-Difluorophenyl)-2,3-dihydro-4-methoxycarbonyl-1-(3-(4-methoxycarbonyl-4-phenylpiperidin-1-yl)prop-1-yl) aminocarbonyl-2(1H)-imidazolone

HRID 1003749Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1003749
ClC(Cl)(Cl)[C:3]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[C:12]([F:17])[CH:11]=2)=[C:8]([C:18]([O:20][CH3:21])=[O:19])[NH:7][C:6]1=[O:22])=[O:4].[NH2:25][CH2:26][CH2:27][CH2:28][N:29]1[CH2:34][CH2:33][C:32]([C:41]([O:43][CH3:44])=[O:42])([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:31][CH2:30]1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[F:17][C:12]1[CH:11]=[C:10]([C:9]2[N:5]([C:3]([NH:25][CH2:26][CH2:27][CH2:28][N:29]3[CH2:30][CH2:31][C:32]([C:41]([O:43][CH3:44])=[O:42])([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[CH2:33][CH2:34]3)=[O:4])[C:6](=[O:22])[NH:7][C:8]=2[C:18]([O:20][CH3:21])=[O:19])[CH:15]=[CH:14][C:13]=1[F:16]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 106838831-(3-Aminopropyl)-4-methoxycarbonyl-4-phenylpiperidineHCID 187982711-trichloroacetyl-5-(3,4-difluorophenyl)-2,3-dihydro-4-methoxycarbonyl-2(1H)-imidazolone

Produkt 1

HCID 187982775-(3,4-Difluorophenyl)-2,3-dihydro-4-methoxycarbonyl-1-(3-(4-methoxycarbonyl-4-phenylpiperidin-1-yl)prop-1-yl) aminocarbonyl-2(1H)-imidazoloneAusbeute 2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 1-trichloroacetyl-5-(3,4-difluorophenyl)-2,3-dihydro-4-methoxycarbonyl-2(1H)-imidazolone (583 mg, 1.46 mmol), 1-(3-aminopropyl)-4-methoxycarbonyl-4-phenylpiperidine (808 mg, 2.92 mmol) and potassium carbonate (809 mg, 5.85 mmol) in dioxane (15 mL) was heated at reflux for 24 hours and then concentrated. The residue was partitioned between EtOAc and water. The organic layer was dried over Na2SO4, filtered and concentrated to give the crude product which was flash chromatographed over silica gel to give the product (15 mg, 2% yield). Hydrochloride salt: light brown solid; m.p. 134-136° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. concentrationconcentrated
  4. customThe residue was partitioned between EtOAc and water
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude product which
  9. customchromatographed over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-9d49694ebe004365942cb81ef6ea5782
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06046331

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