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 23643ノート

反応式

HRID 23643 の反応式
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

参加物

4

反応物 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

生成物 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-carboxamide収率 29%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-cb6ce3eecd4a4f00a12b8967537bdf2c
出典データセット
uspto-grants-2005_02
特許番号
US06852731B2

反応ノート

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