2-Aminothiazole → Ethyl imidazo[2,1-b]thiazole-6-carboxylate

HRID 872788Notes

Reaction equation

HRID 872788 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.Br[CH2:8][C:9](=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11]>COCCOC>[S:3]1[CH:4]=[CH:5][N:6]2[CH:8]=[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:1]=[C:2]12

Participants

4

Reactant 2

HCID 21552-AminothiazoleHCID 66144Ethyl bromopyruvate

Product 1

HCID 7018386Ethyl imidazo[2,1-b]thiazole-6-carboxylate

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To the cold solution of 2-aminothiazole (0.5 g, 4.99 mmol) in 10 mL of DME was added ethyl bromopyruvate (0.783 mL, 6.24 mmol). The resultant mixture was stirred at RT for 30 min. The yellow precipitate obtained was filtered. The solid residue was dissolved in 20 mL of ethanol and refluxed for 8 h. After the completion of the reaction as evidenced by LC-MS, the solvent was removed under vacuum. Residue was added to DCM and washed with sodium bicarbonate solution. The organic solvent was evaporated and the crude product was purified by Combiflash. Yield 0.285 g. 1H NMR (400 MHz; CDCl3): δ 1.42 (t, 3H), 4.41 (q, 2H), 6.98 (d, 1H), 7.47 (d, 1H), 8.09 (s, 1H).

Workup

  1. customThe yellow precipitate obtained
  2. filtrationwas filtered
  3. dissolutionThe solid residue was dissolved in 20 mL of ethanol
  4. temperaturerefluxed for 8 h
  5. customAfter the completion of the reaction
  6. customthe solvent was removed under vacuum
  7. additionResidue was added to DCM
  8. washwashed with sodium bicarbonate solution
  9. customThe organic solvent was evaporated
  10. customthe crude product was purified by Combiflash

Sources & evidence

ORD record
ord-24640c688e844aa1bcaacce3ecd79800
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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