Rac-1-(2-furyl)-2-(methylamino)ethanol → 4-(2-amino-2-oxoethyl)-N-(4-chlorobenzyl)-2-{[[2-(2-furyl)-2-hydroxyethyl](methyl)amino]methyl}-3-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

HRID 23625Notes

Reaction equation

HRID 23625 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([OH:10])[CH2:7][NH:8][CH3:9].[NH2:11][C:12](=[O:38])[CH2:13][N:14]1[CH:19]=[C:18]([C:20]([NH:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)=[O:21])[C:17](=[O:31])[C:16]2[S:32][C:33]([CH2:36]Cl)=[C:34]([CH3:35])[C:15]1=2>>[NH2:11][C:12](=[O:38])[CH2:13][N:14]1[CH:19]=[C:18]([C:20]([NH:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)=[O:21])[C:17](=[O:31])[C:16]2[S:32][C:33]([CH2:36][N:8]([CH2:7][CH:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)[OH:10])[CH3:9])=[C:34]([CH3:35])[C:15]1=2

Participants

3

Reactant 2

HCID 11320981Rac-1-(2-furyl)-2-(methylamino)ethanolHCID 225743174-(2-amino-2-oxoethyl)-N-(4-chlorobenzyl)-2-(chloromethyl)-3-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

Product 1

HCID 225743854-(2-amino-2-oxoethyl)-N-(4-chlorobenzyl)-2-{[[2-(2-furyl)-2-hydroxyethyl](methyl)amino]methyl}-3-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

Procedure

Prepared from 1-(2-furyl)-2-(methylamino)ethanol (Preparation 8) and 4-(2-amino-2-oxoethyl)-N-(4-chlorobenzyl)-2-(chloromethyl)-3-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide by the procedure described for Example 2. Recrystallization from acetonitrile afforded 17 mg of the title compound as a white solid.

Workup

  1. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-21d3cb3659b34991893e45da29e5774e
Source dataset
uspto-grants-2005_02
Patent number
US06852731B2

Reaction notes

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