3-[(allyloxy)methyl]-N-(4-chlorobenzyl)-2-{[[(2R)-2-hydroxy-2-pyridin-2-ylethyl](methyl)amino]methyl}-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide → N-(4-Chlorobenzyl)-3-(hydroxymethyl)-2-{[[(2R)-2-hydroxy-2-pyridin-2-ylethyl](methyl)amino]methyl}-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

HRID 23643Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 23643
C([O:4][CH2:5][C:6]1[C:10]2[N:11]([CH3:27])[CH:12]=[C:13]([C:16]([NH:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)=[O:17])[C:14](=[O:15])[C:9]=2[S:8][C:7]=1[CH2:28][N:29]([CH2:31][C@@H:32]([OH:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=1)[CH3:30])C=C>CO.[Pd]>[Cl:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][NH:18][C:16]([C:13]2[C:14](=[O:15])[C:9]3[S:8][C:7]([CH2:28][N:29]([CH2:31][C@@H:32]([OH:39])[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=4)[CH3:30])=[C:6]([CH2:5][OH:4])[C:10]=3[N:11]([CH3:27])[CH:12]=2)=[O:17])=[CH:25][CH:24]=1

Komponenten

4

Edukt 1

HCID 599852123-[(allyloxy)methyl]-N-(4-chlorobenzyl)-2-{[[(2R)-2-hydroxy-2-pyridin-2-ylethyl](methyl)amino]methyl}-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

Produkt 1

HCID 59985209N-(4-Chlorobenzyl)-3-(hydroxymethyl)-2-{[[(2R)-2-hydroxy-2-pyridin-2-ylethyl](methyl)amino]methyl}-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamideAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 104 mg of 3-[(allyloxy)methyl]-N-(4-chlorobenzyl)-2-{[[(2R)-2-hydroxy-2-pyridin-2-ylethyl](methyl)amino]methyl}-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide and 75 mg of 5% Pd/C in 5 mL of MeOH is stirred and heated at 100° C. in a sealed tube for 3 days, then cooled and filtered through Celite. The filtrate is concentrated under reduced pressure, and the residue flash chromatographed on silica gel using 5% MeOH in CH2Cl2 to afford 28 mg of the title compound as a pale yellow glass. Recrystallization from EtOAc-hexane provides 18 mg of white solid.

Aufarbeitung

  1. temperaturecooled
  2. filtrationfiltered through Celite
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. customthe residue flash chromatographed on silica gel using 5% MeOH in CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-cb6ce3eecd4a4f00a12b8967537bdf2c
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06852731B2

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