Water → (R)-tert-butyl 3-(N-(3-methylpyridin-2-yl)-4-(pyrazolo[1,5-a]pyrimidin-3-yl)benzamido)piperidine-1-carboxylate

HRID 588387Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 588387
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([N:14]([C:32]2[C:37]([CH3:38])=[CH:36][CH:35]=[CH:34][N+:33]=2[O-])[C:15](=[O:31])[C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:23]=[N:24][N:25]4[CH:30]=[CH:29][CH:28]=[N:27][C:26]=34)=[CH:18][CH:17]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(N1CCC[C@@H](NC2C(C)=CC=C[N+]=2[O-])C1)=O)(C)(C)C.B(O)(O)B(O)O.O>C(#N)C>[CH3:38][C:37]1[C:32]([N:14]([C@@H:10]2[CH2:11][CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]2)[C:15](=[O:31])[C:16]2[CH:17]=[CH:18][C:19]([C:22]3[CH:23]=[N:24][N:25]4[CH:30]=[CH:29][CH:28]=[N:27][C:26]=34)=[CH:20][CH:21]=2)=[N:33][CH:34]=[CH:35][CH:36]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 10986154Diboron tetrahydroxideHCID 117652714(R)-2-(N-(1-(tert-butoxycarbonyl)piperidin-3-yl)-4-(pyrazolo[1,5-a]pyrimidin-3-yl)benzamido)-3-methylpyridine 1-oxideHCID 178426682HCID 178426682, Verbindung

Produkt 1

HCID 117652897(R)-tert-butyl 3-(N-(3-methylpyridin-2-yl)-4-(pyrazolo[1,5-a]pyrimidin-3-yl)benzamido)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of the compound from Step 1 (R)-2-(1-(tert-butoxycarbonyl)-piperidin-3-ylamino)-3-methylpyridine 1-oxide (760 mg, 1.44 mmol) in acetonitrile (15 mL) was added tetrahydroxydiboron (387 mg, 4.32 mmol) at room temperature. The reaction was stirred at 60° C. overnight. The resulting mixture was treated with water then extracted with EtOAc (3×30 mL). The combined organic layers were dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure to afford the title compound (760 mg) as a white gum. This material was used in the next step without further purification.

Aufarbeitung

  1. extractionthen extracted with EtOAc (3×30 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-aa8c949b71b445ccb8f91ccf44cfe725
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09227956B2

Notizen zur Reaktion

Wird geladen…