Sodium Bicarbonate → HCID 66818134, Verbindung

HRID 1754911Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1754911
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][N:11]=1)[C:6]([OH:8])=O.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][C:22]([NH2:27])([C:25]#[N:26])[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C([O-])(O)=O.[Na+]>CCO>[C:12]([O:16][C:17]([N:19]1[CH2:20][CH2:21][C:22]([C:25]#[N:26])([NH:27][C:6]([C:5]2[CH:9]=[CH:10][N:11]=[C:3]([O:2][CH3:1])[CH:4]=2)=[O:8])[CH2:23][CH2:24]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 8199422-Methoxyisonicotinic AcidHCID 22091429tert-Butyl 4-amino-4-cyanopiperidine-1-carboxylate

Produkt 1

HCID 66818134HCID 66818134, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride 2,7-hydrate (1.06 g, 3.26 mmol) was added to a solution of 2-methoxy-isonicotinic acid (500 mg, 3.26 mmol) and 4-amino-4-cyano-piperidine-1-carboxylic acid tert-butyl ester (669 mg, 2.97 mmol) in EtOH (8.0 ml) at room temperature, and the mixture was stirred for 46.5 hours. An aqueous NaHCO3 solution was added to the reaction mixture, followed by extraction with AcOEt three times. The organic layers were washed with saturated brine, and then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by column chromatography (CH2Cl2/MeOH=99:1 to 95:5) to give 4-cyano-4-[(2-methoxy-pyridine-4-carbonyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester as a colorless form (901 mg, 84%).

Aufarbeitung

  1. extractionfollowed by extraction with AcOEt three times
  2. washThe organic layers were washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by column chromatography (CH2Cl2/MeOH=99:1 to 95:5)

Quellen und Nachweise

ORD-Eintrag
ord-f3123588ecfb40d1b36e625842acfeb9
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09169254B2

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