Potassium Carbonate → N-(1-{[(2R,5R)-2,5-Dimethylpyrrolidin-1-yl]carbonyl}-5-[4-(trifluoromethyl)phenyl]piperidin-3-yl)benzenecarboxamide

HRID 876327

Reaktionsgleichung

Reaktionsgleichung von HRID 876327
[C:1]1([C:7]([NH:9][CH:10]2[CH2:15][CH:14]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)[CH2:13][N:12]([C:26](OC3C=CC([N+]([O-])=O)=CC=3)=[O:27])[CH2:11]2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:38][C@@H:39]1[CH2:43][CH2:42][C@@H:41]([CH3:44])[NH:40]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:38][C@@H:39]1[CH2:43][CH2:42][C@@H:41]([CH3:44])[N:40]1[C:26]([N:12]1[CH2:13][CH:14]([C:16]2[CH:17]=[CH:18][C:19]([C:22]([F:23])([F:25])[F:24])=[CH:20][CH:21]=2)[CH2:15][CH:10]([NH:9][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:8])[CH2:11]1)=[O:27]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 6417672,5-Dimethylpyrrolidine, (2R,5R)-HCID 667014674-Nitrophenyl 3-[(phenylcarbonyl)amino]-5-[4-(trifluoromethyl)phenyl]piperidine-1-carboxylate

Produkt 1

HCID 66701509N-(1-{[(2R,5R)-2,5-Dimethylpyrrolidin-1-yl]carbonyl}-5-[4-(trifluoromethyl)phenyl]piperidin-3-yl)benzenecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

80 mg (0.16 mmol) of 4-nitrophenyl 3-[(phenylcarbonyl)amino]-5-[4-(trifluoromethyl)phenyl]piperidine-1-carboxylate were initially charged in 1.7 ml of DMF, and 46 mg (0.47 mmol) of (2R,5R)-2,5-dimethylpyrrolidine and 22 mg (0.16 mmol) of potassium carbonate were added. The mixture was reacted in a microwave (Emrys Optimizer) at 150° C. for 15 min. The crude product was then purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient). Yield: 12 mg (15% of theory)

Aufarbeitung

  1. customThe mixture was reacted in a microwave (Emrys Optimizer) at 150° C. for 15 min
  2. customThe crude product was then purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient)

Quellen und Nachweise

ORD-Eintrag
ord-e885d12d431148998792d011cdba7707
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987248B2

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