Ethyl 2-amino-5-ethyl-3-thenoate → HCID 12862363, compound

HRID 1155877Notes

Reaction equation

HRID 1155877 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([NH2:10])=[O:9])=[CH:4][CH:3]=1.[NH2:11][C:12]1[S:13][C:14]([CH2:22][CH3:23])=[CH:15][C:16]=1[C:17](OCC)=[O:18]>C(Cl)(Cl)Cl>[CH2:22]([C:14]1[S:13][C:12]2[N:11]=[C:2]3[CH:3]=[CH:4][C:5]([C:8]([NH2:10])=[O:9])=[CH:6][N:7]3[C:17](=[O:18])[C:16]=2[CH:15]=1)[CH3:23]

Participants

4

Reactant 2

HCID 78263Ethyl 2-amino-5-ethyl-3-thenoateHCID 804566-Chloronicotinamide

Product 1

HCID 12862363HCID 12862363, compoundYield 17.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 6.0 g (0.038 mol) of 6-chloro-3-pyridinecarboxamide (Aldrich Chemical Company) and 8.0 g (0.040 mol) of 2-amino-5-ethyl-3-thiophenecarboxylic acid, ethyl ester (Chemische Berichte, Vol. 99, pages 94-100, 1966) is heated in an oil bath at 180° C. for two hours. The mixture is cooled and then suspended in hot chloroform and filtered to give 1.8 g of 2-ethyl-4-oxo-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carboxamide; mp 278-280° C. after recrystallization from pyridine.

Workup

  1. temperatureThe mixture is cooled
  2. filtrationfiltered

Sources & evidence

ORD record
ord-972bfdaf0fcf49b087e89b5475bd3e35
Source dataset
uspto-grants-1982_06
Patent number
US04332947

Reaction notes

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