3-Aminopyridine → HCID 19978118, compound

HRID 1449519Notes

Reaction equation

HRID 1449519 reaction equation
NC1C=NC=CC=1.C[N:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)C.[ClH:17].[CH3:18][C:19]1[N:23]2[CH2:24][CH2:25][CH2:26][N:27]=[C:22]2[S:21][C:20]=1[C:28]([Cl:30])=[O:29]>N1C=CC=CC=1>[ClH:30].[ClH:17].[CH3:18][C:19]1[N:23]2[CH2:24][CH2:25][CH2:26][N:27]=[C:22]2[S:21][C:20]=1[C:28]([NH:9][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)=[O:29]

Participants

5

Reactant 3

HCID 100093-AminopyridineHCID 218852-DimethylaminopyridineHCID 19978142HCID 19978142, compound

Product 1

HCID 19978118HCID 19978118, compoundYield 211.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 20 ml of pyridine was dissolved 200 mg of 3-aminopyridine. To this solution were added 50 mg of dimethylaminopyridine and 600 mg of 3-methyl-6,7-dihydro-5H-thiazolo[3,2-a]pyrimidine-2-carbonylchloride hydrochloride obtained in Example 28, followed by stirring at room temperature for 20 hours. The reaction mixture was concentrated and to the mixture was added saturated sodium hydrogencarbonate aqueous solution. The mixture was extracted with chloroform. The extact was washed with water and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The residue was dissolved in ethanol. To the solution was added saturated hydrogenchloride diethylether solution. The formed crystals were collected by filtration. This crystals were recrystallized from a mixed solvent of ethanol and diethylether to obtain 300 mg of the titled compound.

Workup

  1. concentrationThe reaction mixture was concentrated and to the mixture
  2. additionwas added saturated sodium hydrogencarbonate aqueous solution
  3. extractionThe mixture was extracted with chloroform
  4. washThe extact was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. dissolutionThe residue was dissolved in ethanol
  8. additionTo the solution was added saturated hydrogenchloride diethylether solution
  9. filtrationThe formed crystals were collected by filtration
  10. customThis crystals were recrystallized from a mixed solvent of ethanol and diethylether

Sources & evidence

ORD record
ord-a0eee428a20d4077b2215be6f49c8800
Source dataset
uspto-grants-1997_02
Patent number
US05599813

Reaction notes

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