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 23643노트

반응식

HRID 23643 반응식
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

참가 물질

4

반응물 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

생성물 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-carboxamide수율 29%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cb6ce3eecd4a4f00a12b8967537bdf2c
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06852731B2

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