Ammonium Chloride → HCID 86672761, Verbindung

HRID 1754910Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1754910
[F:1][C:2]([F:16])([O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=1)[CH:3]([F:5])[F:4].[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][C:27]([NH2:32])([C:30]#[N:31])[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18].C(N(CC)C(C)C)(C)C.[Cl-].[NH4+]>CN(C=O)C>[C:17]([O:21][C:22]([N:24]1[CH2:25][CH2:26][C:27]([C:30]#[N:31])([NH:32][C:11](=[O:13])[C:10]2[CH:9]=[CH:8][C:7]([O:6][C:2]([F:1])([F:16])[CH:3]([F:4])[F:5])=[CH:15][CH:14]=2)[CH2:28][CH2:29]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 27766394-(1,1,2,2-Tetrafluoroethoxy)benzoic acidHCID 22091429tert-Butyl 4-amino-4-cyanopiperidine-1-carboxylate

Produkt 1

HCID 86672761HCID 86672761, VerbindungAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

N,N,N′,N′-Tetramethyl-O-(7-azabenzotriazol-1-yl)uoronium hexafluorophosphate (1.60 g, 4.20 mmol) was added to a solution of 4-(1,1,2,2-tetrafluoro-ethoxy)-benzoic acid (1.00 g, 4.20 mmol), 4-amino-4-cyano-piperidine-1-carboxylic acid tert-butyl ester (995 mg, 4.42 mmol) and N,N-diisopropylethylamine (1.46 ml, 8.39 mmol) in DMF (8.8 ml) at 0° C. The mixture was gradually warmed to room temperature and stirred for 28.5 hours. An aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with ethyl acetate three times. The organic layers were sequentially washed with H2O (×2) and saturated brine, and then dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (hexane:AcOEt=90:10→30:70) to give 4-cyano-4-[4-(1,1,2,2-tetrafluoro-ethoxy)-benzoylamino]-piperidine-1-carboxylic acid tert-butyl ester as a light brown powder (1.60 g, 86%).

Aufarbeitung

  1. extractionfollowed by extraction with ethyl acetate three times
  2. washThe organic layers were sequentially washed with H2O (×2) and saturated brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (hexane:AcOEt=90:10→30:70)

Quellen und Nachweise

ORD-Eintrag
ord-1201384aa0684e1a9a0869406b570194
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09169254B2

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