6-Chloronicotinamide → HCID 12862362, compound

HRID 1155876Notes

Reaction equation

HRID 1155876 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]([CH3:22])=[CH:15][C:16]=1[C:17](OCC)=[O:18]>C(Cl)(Cl)Cl>[CH3:22][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

Participants

4

Reactant 2

HCID 804566-ChloronicotinamideHCID 4062885Ethyl 2-Amino-5-methylthiophene-3-carboxylate

Product 1

HCID 12862362HCID 12862362, compoundYield 6.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
185 °C

Procedure

A mixture of 6.0 g (0.038 mol) of 6-chloro-3-pyridinecarboxamide (Aldrich Chemical Company) and 10.0 g (0.054 mol) of 2-amino-5-methyl-3-thiophenecarboxylic acid, ethyl ester (Chemische Berichte, Vol. 99, pages 94-100, 1966) is heated in an oil bath at 185° C. for one hour then at 135°-140° C. for sixteen hours and finally at 195° C. for six hours. The mixture is cooled and then suspended in hot chloroform and filtered to give 0.6 g of 2-methyl-4-oxo-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carboxamide; mp 350°-354° C. after recrystallization from pyridine.

Workup

  1. waitat 135°-140° C. for sixteen hours
  2. temperatureThe mixture is cooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-56dc5795eb354cfcbef00b6a4d792400
Source dataset
uspto-grants-1982_06
Patent number
US04332947

Reaction notes

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