Pyridine → Piperidin-3-yl(methyl)carbamate

HRID 1923907Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1923907
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:7](Cl)(=O)C(C)C.[C:13](=[O:23])([O:15]CC1CCCNC1)[NH2:14].[Li+].[OH-]>CN1C(=O)CCC1.CC#N.O.C(Cl)Cl.O>[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([O:15][C:13](=[O:23])[NH:14][CH3:7])[CH2:2]1

Komponenten

9

Edukt 4

HCID 1049PyridineHCID 3939Lithium HydroxideHCID 62325Isobutyryl chlorideHCID 19082825HCID 19082825, Verbindung

Produkt 1

HCID 81908379Piperidin-3-yl(methyl)carbamateAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittelHCID 18373917Acetonitrile--water (1/1)Lösungsmittel

Versuchsvorschrift

Pyridine (1 mL) and isobutyryl chloride (0.421 g, 3.95 mmol) were added to (R)-tert-butyl 1-(3-amino-5-chloro-1H-pyrrolo [2, 3-1)]pyridin-4-yl)piperidin-3-yl(methyl) carbamate (0.300 g, 0.790 mmol; Example 112, Step A) in NMP (2 mL), and the reaction was stirred at room temperature for 1 hour. 3M aqueous LiOH (3 mL) was then added, and the reaction was stirred for 10 minutes. Water (10 mL) and DCM (10 mL) were then added, and the organic layer was separated, dried, filtered and concentrated. The crude residue was purified by reverse phase chromatography (Biotage SP4, C-18 12M+, 5-95% CH3CN/water) to give (R)-tert-butyl 1-(5-chloro-3-isobutyramido-1H-pyrrolo[2, 3-1)]pyridin-4-yl)piperidin-3-yl(methyl)carbamate (0.180 g, 51% yield).

Aufarbeitung

  1. stirringthe reaction was stirred for 10 minutes
  2. customthe organic layer was separated
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by reverse phase chromatography (Biotage SP4

Quellen und Nachweise

ORD-Eintrag
ord-296de4787fce440da8f6a6539a793ec3
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178131B2

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