Ethanolamine → N-(2-Hydroxyethyl)-3-[(phenylcarbonyl)amino]-5-[4-(trifluoromethyl)phenyl]piperidine-1-carboxamide

HRID 876329

Reaktionsgleichung

Reaktionsgleichung von HRID 876329
[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]([O:28]C3C=CC([N+]([O-])=O)=CC=3)=O)[CH2:11]2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:38][CH2:39][CH2:40][OH:41].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[OH:41][CH2:40][CH2:39][NH:38][C:26]([N:12]1[CH2:13][CH:14]([C:16]2[CH:17]=[CH:18][C:19]([C:22]([F:23])([F:24])[F:25])=[CH:20][CH:21]=2)[CH2:15][CH:10]([NH:9][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:8])[CH2:11]1)=[O:28]

Komponenten

5

Edukt 3

HCID 700EthanolamineHCID 11430Potassium CarbonateHCID 667014674-Nitrophenyl 3-[(phenylcarbonyl)amino]-5-[4-(trifluoromethyl)phenyl]piperidine-1-carboxylate

Produkt 1

HCID 66762428N-(2-Hydroxyethyl)-3-[(phenylcarbonyl)amino]-5-[4-(trifluoromethyl)phenyl]piperidine-1-carboxamide

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 29 mg (0.47 mmol) of 2-aminoethanol 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: 10 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-d36f83c3c1ee4ac98ed66dca97d790d1
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987248B2

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