2,4,6-Trimethylpyridine → N-[(4-chlorophenyl)methyl]-7-methyl-4-oxo-2-(thiomorpholinomethyl)thieno[2,3-b]pyridine-5-carboxamide

HRID 2299307

Reaktionsgleichung

Reaktionsgleichung von HRID 2299307
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:22])[C:12]3[CH:19]=[C:18]([CH2:20]O)[S:17][C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1.N1C(C)=CC(C)=CC=1C.CS(Cl)(=O)=O.[NH:39]1[CH2:44][CH2:43][S:42][CH2:41][CH2:40]1>CN(C=O)C.CN(C1C=CN=CC=1)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:22])[C:12]3[CH:19]=[C:18]([CH2:20][N:39]4[CH2:44][CH2:43][S:42][CH2:41][CH2:40]4)[S:17][C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:23][CH:24]=1

Komponenten

8

Edukt 4

HCID 79532,4,6-TrimethylpyridineHCID 31297Methanesulfonyl chlorideHCID 67164ThiomorpholineHCID 6482399N-[(4-chlorophenyl)methyl]-2-(hydroxymethyl)-7-methyl-4-oxo-thieno[2,3-b]pyridine-5-carboxamide

Produkt 1

HCID 6482405N-[(4-chlorophenyl)methyl]-7-methyl-4-oxo-2-(thiomorpholinomethyl)thieno[2,3-b]pyridine-5-carboxamideAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of N-(4-chlorobenzyl)-2-(hydroxymethyl)-7-methyl-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide (0.300 g) from Example No. 35 in DMF (16 mL) are added DMAP (16 mg), 2,4,6-collidine (0.27 mL), and methanesulfonyl chloride (0.16 mL). The reaction mixture is stirred at room temperature for 2 h and then thiomorpholine (0.83 mL) is added. The mixture is stirred at room temperature for 3 d and is then poured into water (50 mL). The resulting off-white solid is filtered off and recrystallized from ethanol to yield 0.222 g (60%) of the title compound as an off-white solid.

Aufarbeitung

  1. stirringThe mixture is stirred at room temperature for 3 d
  2. filtrationThe resulting off-white solid is filtered off
  3. customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-d5b8f3e1664f4b5d9d2127923397e6d5
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06495683B2

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