6-Chloronicotinamide → HCID 12953063, compound

HRID 904553Notes

Reaction equation

HRID 904553 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([O:11]C)=O)=[C:4]([CH3:8])[S:5][C:6]=1[CH3:7].Cl[C:14]1[N:19]=[CH:18][C:17]([C:20]([NH2:22])=[O:21])=[CH:16][CH:15]=1>N1C=CC=CC=1>[CH3:8][C:4]1[S:5][C:6]([CH3:7])=[C:2]2[C:3]=1[C:9](=[O:11])[N:19]1[CH:18]=[C:17]([C:20]([NH2:22])=[O:21])[CH:16]=[CH:15][C:14]1=[N:1]2

Participants

4

Reactant 2

HCID 804566-ChloronicotinamideHCID 11019562Methyl 4-amino-2,5-dimethylthiophene-3-carboxylate

Product 1

HCID 12953063HCID 12953063, compoundYield 3.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 5 g (0.0226 mol) of 4-amino-2,5-dimethyl-3-thiophenecarboxylic acid, methyl ester and 3.5 g (0.0226 mol) of 6-chloro-3-pyridinecarboxamide (Aldrich Chemical Company) is heated in an oil bath at 180° C. for thirty minutes. The mixture is cooled, dissolved in hot pyridine, cooled, the precipitate collected and dissolved in hot methanol, activated charcoal (Darco-G60, Matheson, Coleman and Bell) is added and the hot suspension is filtered through Supercell Hyflo® (Johns-Manville). The filtrate is cooled to give 0.2 g of 1,3-dimethyl-10-oxo-10H-pyrido[1,2-a]thieno[3,4-d]pyrimidine-7-carboxamide with methanol (1:0.125); mp 272°-275° C. after recrystallization from methanol.

Workup

  1. temperatureThe mixture is cooled
  2. temperaturecooled
  3. customthe precipitate collected
  4. dissolutiondissolved in hot methanol
  5. additionactivated charcoal (Darco-G60, Matheson, Coleman and Bell) is added
  6. filtrationthe hot suspension is filtered through Supercell Hyflo® (Johns-Manville)
  7. temperatureThe filtrate is cooled

Sources & evidence

ORD record
ord-94f4a169c92e46cea3189579546c7015
Source dataset
uspto-grants-1980_10
Patent number
US04230707

Reaction notes

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