2,4,6-Trimethylpyridine → N-(4-chlorobenzyl)-7-methyl-2-(4-morpholinylmethyl)-4-oxo-4,7-dihydrothieno(2,3-b)pyridine-5-carboxamide

HRID 1978958

Reaktionsgleichung

Reaktionsgleichung von HRID 1978958
[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][O: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][O: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 8083MorpholineHCID 31297Methanesulfonyl chlorideHCID 6482399N-[(4-chlorophenyl)methyl]-2-(hydroxymethyl)-7-methyl-4-oxo-thieno[2,3-b]pyridine-5-carboxamide

Produkt 1

HCID 503580N-(4-chlorobenzyl)-7-methyl-2-(4-morpholinylmethyl)-4-oxo-4,7-dihydrothieno(2,3-b)pyridine-5-carboxamideAusbeute 81,3 %

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 (0.250 g) from Example No. 35 in DMF (14 mL) are added DMAP (13 mg), 2,4,6-collidine (0.23 mL), and methanesulfonyl chloride (0.13 mL). The reaction is stirred at rt for 1.5 h and then morpholine (0.60 mL, 6.9 mmol) is added. The reaction is stirred at rt for 18 h. The reaction mixture is poured into water (40 mL). The resulting off-white solid is filtered off and recrystallized from ethanol to yield 0.242 g (81%) of the title compound as an off-white, crystalline solid.

Aufarbeitung

  1. stirringThe reaction is stirred at rt for 18 h
  2. filtrationThe resulting off-white solid is filtered off
  3. customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-9cbd679a5c354723979f9793ea79c779
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06239142B1

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