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(S)-3-[6-(2-methoxy-phenyl)-pyrimidin-4-ylcarbamoyl]-piperidine-1-carboxylic acid benzyl ester → (S)-piperidine-3-carboxylic acid [6-(2-methoxy-phenyl)-pyrimidin-4-yl]-amide

HRID 1020058
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1020058
C(OC([N:11]1[CH2:16][CH2:15][CH2:14][C@H:13]([C:17](=[O:33])[NH:18][C:19]2[CH:24]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[O:31][CH3:32])[N:22]=[CH:21][N:20]=2)[CH2:12]1)=O)C1C=CC=CC=1>CO.[OH-].[Pd+2].[OH-]>[CH3:32][O:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[C:23]1[N:22]=[CH:21][N:20]=[C:19]([NH:18][C:17]([C@H:13]2[CH2:14][CH2:15][CH2:16][NH:11][CH2:12]2)=[O:33])[CH:24]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 1

HCID 59509033(S)-3-[6-(2-methoxy-phenyl)-pyrimidin-4-ylcarbamoyl]-piperidine-1-carboxylic acid benzyl ester

Produkt 1

HCID 59508991(S)-piperidine-3-carboxylic acid [6-(2-methoxy-phenyl)-pyrimidin-4-yl]-amideAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of (S)-3-[6-(2-methoxy-phenyl)-pyrimidin-4-ylcarbamoyl]-piperidine-1-carboxylic acid benzyl ester (XXXIV) (7.0 g) in 50 ml of methanol was added 10% palladium hydroxide (1.5 g) under an atmosphere of nitrogen and the mixture was stirred at room temperature under an atmosphere of hydrogen for 8 hours. The reaction mixture was filtered through celite and the solvent was evaporated. The obtained product was taken in diethyl ether, stirred, filtered, washed with diethyl ether and dried under vacuum to obtain (S)-piperidine-3-carboxylic acid [6-(2-methoxy-phenyl)-pyrimidin-4-yl]-amide (compound #17A) as a white solid (3.0 g, 62%), melting point 163-165° C.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe solvent was evaporated
  3. stirringstirred
  4. filtrationfiltered
  5. washwashed with diethyl ether
  6. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-e84d6f71bdcc428bb1d9108d3eb8d0aa
Quelldatensatz
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08716296B2

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