HCID 12862390, compound → HCID 178440585, compound

HRID 904545Notes

Reaction equation

HRID 904545 reaction equation
[CH2:1]([C:5]1[S:9][C:8]([NH:10][C:11]2[N:16]=[CH:15][C:14]([C:17]([OH:19])=O)=[CH:13][CH:12]=2)=[C:7]([C:20]([OH:22])=O)[CH:6]=1)[CH2:2][CH2:3][CH3:4].O.[NH2:24][C:25]1[NH:29][N:28]=[N:27][N:26]=1>CN(C)C=O>[CH2:1]([C:5]1[S:9][C:8]2[N:10]=[C:11]3[CH:12]=[CH:13][C:14]([C:17]([NH:24][C:25]4[NH:29][N:28]=[N:27][N:26]=4)=[O:19])=[CH:15][N:16]3[C:20](=[O:22])[C:7]=2[CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 12862390HCID 12862390, compoundHCID 178509300HCID 178509300, compound

Product 1

HCID 178440585HCID 178440585, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-[(5-butyl-3-carboxy-2-thienyl)amino]-3-pyridinecarboxylic acid (Example 39), 3.2 g (0.01 mol) and 9.93 g (0.06 mol) of 1, 11 -carbonyldiimidazole (Aldrich Chemical Company) in 100 ml of dimethylformamide is heated in a wax bath under a nitrogen atmosphere with stirring at 100° to 108° C. for seventy minutes, cooled and stirred at room temperature for one hour. To the previous mixture is added 5-aminotetrazole monohydrate (Aldrich Chemical Company), 2.06 g (0.02 mol) and the mixture is heated at 100°-108° C. for ninety minutes. The solvent is evaporated and the residue dissolved in dimethylformamide, filtered, cooled and the precipitate collected and washed with methanol to give 1.2 g of 2-butyl-4-oxo-N-1H-tetrazol-5-yl-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carboxamide; mp 293° C. (dec) after recrystallization from pyridine.

Workup

  1. temperatureis heated in a wax bath under a nitrogen atmosphere
  2. temperaturecooled
  3. stirringstirred at room temperature for one hour
  4. temperaturethe mixture is heated at 100°-108° C. for ninety minutes
  5. customThe solvent is evaporated
  6. dissolutionthe residue dissolved in dimethylformamide
  7. filtrationfiltered
  8. temperaturecooled
  9. customthe precipitate collected
  10. washwashed with methanol

Sources & evidence

ORD record
ord-14e28531d1624081bfb3decbb57a595d
Source dataset
uspto-grants-1980_10
Patent number
US04230707

Reaction notes

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