Water → 4-(2-amino-2-oxoethyl)-N-(4-chlorobenzyl)-2-(hydroxymethyl)-3-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

HRID 23623

Reaktionsgleichung

Reaktionsgleichung von HRID 23623
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11]([OH:22])=[C:12]3[S:18][C:17]([CH2:19][OH:20])=[C:16]([CH3:21])[C:13]3=[N:14][CH:15]=2)=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:32][C:33]([NH2:35])=[O:34].O>CN(C=O)C>[NH2:35][C:33](=[O:34])[CH2:32][N:14]1[CH:15]=[C:10]([C:8]([NH:7][CH2:6][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:24][CH:23]=2)=[O:9])[C:11](=[O:22])[C:12]2[S:18][C:17]([CH2:19][OH:20])=[C:16]([CH3:21])[C:13]1=2

Komponenten

6

Edukt 4

HCID 962WaterHCID 3727Iodoacetamide2×HCID 11430Potassium Carbonate2×HCID 178429625HCID 178429625, Verbindung

Produkt 1

HCID 225743684-(2-amino-2-oxoethyl)-N-(4-chlorobenzyl)-2-(hydroxymethyl)-3-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamideAusbeute 56,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of N-(4-chlorobenzyl)-7-hydroxy-2-(hydroxymethyl)-3-methylthieno[3,2-b]pyridine-6-carboxamide (100 mg, 0.276 mmol), potassium carbonate (57 mg, 0.41 mmol) and iodoacetamide (255 mg, 1.38 mmol) in DMF (1.5 mL) was stirred at 50° C. for 18 hrs. Additional iodoacetamide (255 mg) and potassium carbonate (57 mg) were added, and the reaction was stirred at the same temperature for another 12 hrs. After cooling, cold water was added, and the resulting ppt was collected by filtration after chilling in an ice bath. The collected crude solid was recrystallized from aq. ethanol to give the title compound (65 mg) as a lt. brown solid.

Aufarbeitung

  1. stirringthe reaction was stirred at the same temperature for another 12 hrs
  2. temperatureAfter cooling
  3. filtrationthe resulting ppt was collected by filtration
  4. temperatureafter chilling in an ice bath
  5. customThe collected crude solid
  6. customwas recrystallized from aq. ethanol

Quellen und Nachweise

ORD-Eintrag
ord-a2a3ee5c1f5d4061bd2b4e9afb037b1c
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06852731B2

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