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 23643Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-cb6ce3eecd4a4f00a12b8967537bdf2c
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06852731B2

Reaction notes

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