Methyl 2-chloro-3-oxopentanoate → Methyl 8-(cyclohexylmethoxy)-2-ethylimidazo[1,2-a]pyridine-3-carboxylate

HRID 1844155Notes

Reaction equation

HRID 1844155 reaction equation
[CH:1]1([CH2:7][O:8][C:9]2[C:10]([NH2:15])=[N:11][CH:12]=[CH:13][CH:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH:17]([C:22](=O)[CH2:23][CH3:24])[C:18]([O:20][CH3:21])=[O:19]>C(O)C>[CH:1]1([CH2:7][O:8][C:9]2[C:10]3[N:11]([C:17]([C:18]([O:20][CH3:21])=[O:19])=[C:22]([CH2:23][CH3:24])[N:15]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 545096Methyl 2-chloro-3-oxopentanoateHCID 138258903-(Cyclohexylmethoxy)pyridin-2-amine

Product 1

HCID 86718180Methyl 8-(cyclohexylmethoxy)-2-ethylimidazo[1,2-a]pyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 100 mg (0.485 mmol) of 3-(cyclohexylmethoxy)pyridine-2-amine and 399 mg (2.42 mmol) of methyl 2-chloro-3-oxopentanoate in 4 ml of ethanol was heated at reflux overnight. The mixture was then cooled and concentrated and the residue obtained was purified by preparative HPLC (Method 6). This gave 26 mg (17% of theory) of methyl 8-(cyclohexylmethoxy)-2-ethylimidazo[1,2-a]pyridine-3-carboxylate.

Workup

  1. temperatureat reflux overnight
  2. temperatureThe mixture was then cooled
  3. concentrationconcentrated
  4. customthe residue obtained
  5. customwas purified by preparative HPLC (Method 6)

Sources & evidence

ORD record
ord-d0117513d9bb4fd3b938580eaaa62c5f
Source dataset
uspto-grants-2015_02
Patent number
US08946215B2

Reaction notes

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