Diisopropylethylamine → N-(4-chlorobenzyl)-2-{[[2-hydroxy-2-(1-oxidopyridin-3-yl)ethyl](methyl)amino]methyl}-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

HRID 23627

Reaktionsgleichung

Reaktionsgleichung von HRID 23627
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:23])[C:12]3[S:19][C:18]([CH2:20]Cl)=[C:17]([CH3:22])[C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1.[CH3:26][NH:27][CH2:28][CH:29]([C:31]1[CH:32]=[N+:33]([O-:37])[CH:34]=[CH:35][CH:36]=1)[OH:30].C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:23])[C:12]3[S:19][C:18]([CH2:20][N:27]([CH2:28][CH:29]([OH:30])[C:31]4[CH:32]=[N+:33]([O-:37])[CH:34]=[CH:35][CH:36]=4)[CH3:26])=[C:17]([CH3:22])[C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:24][CH:25]=1

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 225743152-(Methylamino)-1-(1-oxidopyridin-3-yl)ethanolHCID 22574363N-(4-chlorobenzyl)-2-(chloromethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

Produkt 1

HCID 22574316N-(4-chlorobenzyl)-2-{[[2-hydroxy-2-(1-oxidopyridin-3-yl)ethyl](methyl)amino]methyl}-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamideAusbeute 59,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of N-(4-chlorobenzyl)-2-(chloromethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide (135 mg, 0.342 mmol), 2-(methylamino)-1-(1-oxidopyridin-3-yl)ethanol (Preparation 86, 69 mg, 0.50 mmol) and diisopropylethylamine (89 μL, 0.51 mmol) in dry DMF (5.0 mL) was stirred for 20 hours at room temperature. The solution was then diluted with water (20 mL). The resulting precipitate was collected by filtration and the collected solid was dried in vacuo, providing 107 mg of the titled compound as a white solid.

Aufarbeitung

  1. filtrationThe resulting precipitate was collected by filtration
  2. customthe collected solid was dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-45faeedd0f14429585b25d393e3512f8
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06852731B2

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