2-Aminopyridine → HCID 20145048, compound

HRID 648579Notes

Reaction equation

HRID 648579 reaction equation
Br[CH2:2][C:3]([C:5]1[S:9][C:8]([NH:10][CH3:11])=[N:7][C:6]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])=O.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1>C(#N)C>[CH2:15]([O:14][C:12]([C:6]1[N:7]=[C:8]([NH:10][CH3:11])[S:9][C:5]=1[C:3]1[N:17]=[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]2[CH:2]=1)=[O:13])[CH3:16]

Participants

4

Reactant 2

HCID 104392-AminopyridineHCID 20145020HCID 20145020, compound

Product 1

HCID 20145048HCID 20145048, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of ethyl 5-(2-bromoacetyl)-2-methylamino-4-thiazolecarboxylate (2.5 g) and 2-aminopyridine (2.3 g) in acetonitrile (100 ml) was refluxed for 1.5 hours. The reaction mixture was evaporated in vacuo. To the residue was added water and ethyl acetate and the resulting mixture was acidified to pH 0.8 with 10% hydrochloric acid. The separated aqueous layer was adjusted to pH 7.0 with 20% aqueous potassium carbonate and extracted with a mixture of ethyl acetate and tetrahydrofuran. The organic extract was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was recrystallized from a mixture of ethyl acetate and tetrahydrofuran to give 2-(4-ethoxycarbonyl-2-methylamino-5-thiazolyl)imidazo[1,2-a]pyridine (1.5 g). mp 197°-200° C.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. additionTo the residue was added water and ethyl acetate
  3. extractionextracted with a mixture of ethyl acetate and tetrahydrofuran
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was recrystallized from a mixture of ethyl acetate and tetrahydrofuran

Sources & evidence

ORD record
ord-1cad244e237449cf8bcd03fdc5376615
Source dataset
uspto-grants-1988_04
Patent number
US04735957

Reaction notes

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