Potassium Carbonate → HCID 20145022, compound

HRID 648580Notes

Reaction equation

HRID 648580 reaction equation
[CH3:1][NH:2][C:3]1[S:4][C:5]([C:13](=O)[CH:14](Br)[CH3:15])=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:7]=1.[CH3:18][C:19]1[CH:20]=[CH:21][C:22]([NH2:25])=[N:23][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.Cl.C(OCC)(=O)C>[CH2:11]([O:10][C:8]([C:6]1[N:7]=[C:3]([NH:2][CH3:1])[S:4][C:5]=1[C:13]1[N:25]=[C:22]2[CH:21]=[CH:20][C:19]([CH3:18])=[CH:24][N:23]2[C:14]=1[CH3:15])=[O:9])[CH3:12]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 153482-Amino-5-methylpyridineHCID 20145007HCID 20145007, compound

Product 1

HCID 20145022HCID 20145022, compoundYield 57.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethyl 2-methylamino-5-(2-bromopropionyl)-4-thiazolecarboxylate (2.2 g) and 5-methyl-2-aminopyridine (2.6 g) in acetonitrile (80 ml) was refluxed for 2 hours. The reaction mixture was evaporated to afford a residue, which was dissolved in a mixture of 5% hydrochloric acid and ethyl acetate. The separated aqueous solution was adjusted to pH 8.0 with 20% potassium carbonate and extracted with ethyl acetate. The extract was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo to afford a crystalline residue, which was recrystallized from a mixture of ethyl acetate and diethyl ether to give 2-(4-ethoxycarbonyl-2-methylaminothiazol-5-yl)-3,6-dimethylimidazo[1,2-a]pyridine (1.3 g).

Workup

  1. customThe reaction mixture was evaporated
  2. customto afford a residue, which
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated in vacuo
  7. customto afford a crystalline residue, which
  8. customwas recrystallized from a mixture of ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-1c1730b221d841dc9c98a7616d1c8cd2
Source dataset
uspto-grants-1988_04
Patent number
US04735957

Reaction notes

Loading…