6-Chloronicotinamide → HCID 12862365, compound

HRID 1155870Notes

Reaction equation

HRID 1155870 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]([CH:22]([CH3:24])[CH3:23])=[CH:15][C:16]=1[C:17](OCC)=[O:18]>CO>[CH3:24][CH: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 804566-ChloronicotinamideHCID 2756461ethyl 2-amino-5-isopropylthiophene-3-carboxylate

Product 1

HCID 12862365HCID 12862365, compoundYield 20.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 24.0 g (0.1538 mol) of 6-chloro-3-pyridinecarboxamide (Aldrich Chemical Company) and 32.8 g (0.1538 mol) of 2-amino-5-(1-methylethyl)-3-thiophenecarboxylic acid, ethyl ester (Tetrahedron, Vol. 33, pages 2089-2092, 1977) is heated in a wax bath at 178°-182° C. for two hundred five minutes and then at 180°-196° C. for sixty-five minutes under nitrogen. The mixture is cooled, suspended in hot methanol and filtered to give 8.9 g of 2-(1-methylethyl)-4-oxo-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carboxamide; mp 280°-282° C. after recrystallization from dimethylformamide.

Workup

  1. temperatureis heated in a wax bath at 178°-182° C. for two hundred five minutes
  2. waitat 180°-196° C. for sixty-five minutes under nitrogen
  3. temperatureThe mixture is cooled
  4. filtrationfiltered

Sources & evidence

ORD record
ord-9f14ba36e080419387788b59968d3b94
Source dataset
uspto-grants-1982_06
Patent number
US04332947

Reaction notes

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