2,4,6-Trimethylpyridine → N-(4-chlorobenzyl)-2-(chloromethyl)-7-propyl-4-oxo4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide

HRID 2307295Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2307295
N1C(C)=CC(C)=CC=1C.CS([Cl:14])(=O)=O.[Cl:15][C:16]1[CH:40]=[CH:39][C:19]([CH2:20][NH:21][C:22]([C:24]2[C:25](=[O:38])[C:26]3[CH:35]=[C:34]([CH2:36]O)[S:33][C:27]=3[N:28]([CH2:30][CH2:31][CH3:32])[CH:29]=2)=[O:23])=[CH:18][CH:17]=1>CN(C=O)C.O>[Cl:15][C:16]1[CH:40]=[CH:39][C:19]([CH2:20][NH:21][C:22]([C:24]2[C:25](=[O:38])[C:26]3[CH:35]=[C:34]([CH2:36][Cl:14])[S:33][C:27]=3[N:28]([CH2:30][CH2:31][CH3:32])[CH:29]=2)=[O:23])=[CH:18][CH:17]=1

Komponenten

6

Edukt 3

HCID 79532,4,6-TrimethylpyridineHCID 31297Methanesulfonyl chlorideHCID 22605728N-(4-chlorobenzyl)-7-propyl-2-(hydroxymethyl)-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide

Produkt 1

HCID 22605695N-(4-chlorobenzyl)-2-(chloromethyl)-7-propyl-4-oxo4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-N,N-Dimethylaminopyridine (80 mg), 2,4,6-collidine (1.39 mL), and methanesulfonyl chloride (0.81 mL) are added to a solution of N-(4-chlorobenzyl)-7-propyl-2-(hydroxymethyl)-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide (Preparation 12, 1.63 g) in anhydrous DMF (80 mL). The reaction mixture is stirred at room temperature for 24 h. The mixture is diluted with water (150 mL) and filtered. The resulting light yellow powder is recrystallized from acetonitrile and dried in a vacuum oven to afford 1.4 g of the title compound as a light yellow solid. Physical characteristics. Mp 186.5-188° C.; 1H NMR (300 Mhz,7 DMSO-6) δ 10.45, 8.75, 7.56, 7.39, 5.15, 4.54, 4.27, 1.85, 0.91. Anal. Found: C, 55.76; H, 4.59; N, 6.95; Cl, 16.88; S, 7.80.

Aufarbeitung

  1. filtrationfiltered
  2. customThe resulting light yellow powder is recrystallized from acetonitrile
  3. customdried in a vacuum oven

Quellen und Nachweise

ORD-Eintrag
ord-c5f816fcff8b429c87a50de413586b84
Quelldatensatz
uspto-grants-2004_12
Patentnummer
US06831081B2

Notizen zur Reaktion

Wird geladen…