(3R)-3-Aminopiperidine, 3-BOC protected → tert-butyl (R)-1-(5-bromo-3-(trans-2-phenyl cyclopropanecarboxamido)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-ylcarbamate

HRID 408432

Reaktionsgleichung

Reaktionsgleichung von HRID 408432
[Br:1][C:2]1[C:3](F)=[C:4]2[C:10]([NH:11][C:12]([C@@H:14]3[CH2:16][C@H:15]3[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:13])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[NH:24]1[CH2:29][CH2:28][CH2:27][C@@H:26]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:25]1>C(O)(CC)C>[Br:1][C:2]1[C:3]([N:24]2[CH2:29][CH2:28][CH2:27][C@@H:26]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:35])([CH3:34])[CH3:36])[CH2:25]2)=[C:4]2[C:10]([NH:11][C:12]([C@@H:14]3[CH2:16][C@H:15]3[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:13])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 1514172(3R)-3-Aminopiperidine, 3-BOC protectedHCID 67045175trans-N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-phenylcyclopropanecarboxamide

Produkt 1

HCID 86652144tert-butyl (R)-1-(5-bromo-3-(trans-2-phenyl cyclopropanecarboxamido)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-ylcarbamateAusbeute 48,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6568(+-)-2-ButanolLösungsmittel

Versuchsvorschrift

trans-N-(5-Bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-phenylcyclopropanecarboxamide (500 mg, 1.34 mmol) and (R)-tert-butyl piperidin-3-ylcarbamate (1338 mg, 6.68 mmol) in s-BuOH (5 mL) were heated to 135° C. in a sealed tube for 24 hours. After cooling down, the residue was concentrated and purified by reverse phase chromatography (SP4, 25M, water/ACN 80/20→0/100, 30 CV) to yield tert-butyl (R)-1-(5-bromo-3-(trans-2-phenylcyclopropanecarboxamido)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-ylcarbamate (359 mg, 48.5% yield) as a solid.

Aufarbeitung

  1. temperatureAfter cooling down
  2. concentrationthe residue was concentrated
  3. custompurified by reverse phase chromatography (SP4, 25M, water/ACN 80/20→0/100, 30 CV)

Quellen und Nachweise

ORD-Eintrag
ord-07b7a0cb0ee141d49717aa80f3074138
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08758830B2

Verknüpfte Notizen

Wird geladen…