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

HRID 23629

Reaktionsgleichung

Reaktionsgleichung von HRID 23629
[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.[O:26]1[C:31]2[CH:32]=[CH:33][C:34]([CH:36]([OH:40])[CH2:37][NH:38][CH3:39])=[CH:35][C:30]=2[O:29][CH2:28][CH2:27]1.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:38]([CH2:37][CH:36]([C:34]4[CH:33]=[CH:32][C:31]5[O:26][CH2:27][CH2:28][O:29][C:30]=5[CH:35]=4)[OH:40])[CH3:39])=[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 225743001-(2,3-Dihydro-1,4-benzodioxin-6-yl)-2-(methylamino)ethan-1-olHCID 22574363N-(4-chlorobenzyl)-2-(chloromethyl)-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

Produkt 1

HCID 10289807N-(4-chlorobenzyl)-2-{[[2-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-hydroxyethyl](methyl)amino]methyl}-3,4-dimethyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamideAusbeute 73,1 %

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 (100 mg, 0.253 mmol), 1-(1,4-benzodioxan-6-yl)-2-(methylamino)ethanol (Preparation 13, 79 mg, 0.38 mmol), and diisopropylethylamine (66 μL, 0.38 mmol) in dry DMF (5.5 mL) was stirred at room temperature for 18 hours. The solution was then diluted with water (20 mL). The resulting precipitate was collected by filtration and the collected solid was dried in vacuo at 60° C. to provide the titled compound (105 mg) as an off white solid.

Aufarbeitung

  1. filtrationThe resulting precipitate was collected by filtration
  2. customthe collected solid was dried in vacuo at 60° C.

Quellen und Nachweise

ORD-Eintrag
ord-1150ca91e56143a0a81167459b8a350f
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06852731B2

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