Triethyl orthoacetate → HCID 121386245, compound

HRID 2202950Notes

Reaction equation

HRID 2202950 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH3:15])=[C:9]([C:11]([NH:13][NH2:14])=[O:12])[N:10]=2)[CH:7]=1.[C:16](OCC)(OCC)(OCC)[CH3:17]>CC(O)=O>[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH3:15])=[C:9]([C:11]3[O:12][C:16]([CH3:17])=[N:14][N:13]=3)[N:10]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 66221Triethyl orthoacetateHCID 89690276HCID 89690276, compound

Product 1

HCID 121386245HCID 121386245, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 6-iodo-3-methylimidazo[1,2-a]pyridine-2-carbohydrazide (200 mg) in AcOH (0.5 ml) was added triethyl orthoacetate (2 ml) at room temperature, and the reaction mixture was heated at reflux for 4 h. The mixture was then cooled to room temperature, and the reaction mixture was concentrated in vacuo. The residue was diluted with EtOAc, and the EtOAc layer was washed with water and brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM) to give the title compound (100 mg) as a light yellow solid.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 4 h
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. additionThe residue was diluted with EtOAc
  5. washthe EtOAc layer was washed with water and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-4307af94c35640099fa525f71fc34d6c
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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