Acetic Acid → 1-(3-Methyl[1,2,4]triazolo[4,3-a]pyridin-6-yl)cyclopropanecarboxylic acid

HRID 1099050Notes

Reaction equation

HRID 1099050 reaction equation
[NH:1]([C:3]1[N:8]=[CH:7][C:6]([C:9]2([C:12]([O:14]C)=[O:13])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)[NH2:2].[CH:16](=O)[CH3:17].C(O)(=O)C.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>C(O)C>[CH3:16][C:17]1[N:8]2[CH:7]=[C:6]([C:9]3([C:12]([OH:14])=[O:13])[CH2:11][CH2:10]3)[CH:5]=[CH:4][C:3]2=[N:1][N:2]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 12217721Iodo benzene diacetateHCID 59216299Methyl 1-(6-hydrazinopyridin-3-yl)cyclopropanecarboxylate

Product 1

HCID 592162871-(3-Methyl[1,2,4]triazolo[4,3-a]pyridin-6-yl)cyclopropanecarboxylic acidYield 30.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl 1-(6-hydrazinopyridin-3-yl)cyclopropanecarboxylate (150 mg, 0.72 mol) in ethanol (3 mL) was added acetaldehyde (33.5 mg, 0.760 mmol) and acetic acid (41 μL, 0.72 mmol). The mixture was stirred at RT for 2 h, and then concentrated to dryness. The residue was dissolved in methylene chloride (3 mL), and iodobenzene diacetate (256 mg, 0.796 mmol) was added dropwise. The reaction mixture was stirred at RT overnight. The reaction solution was concentrated to dryness. The residue was purified through silica gel chromatograph using 10% MeOH in CH2Cl2 to afford the desired compound (50 mg, 30%). Analytical LCMS: (M+H)+=218.0.

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionThe residue was dissolved in methylene chloride (3 mL)
  3. stirringThe reaction mixture was stirred at RT overnight
  4. concentrationThe reaction solution was concentrated to dryness
  5. customThe residue was purified through silica gel chromatograph

Sources & evidence

ORD record
ord-6cbe1eab8f8b4dfcaf54b1625b540d60
Source dataset
uspto-grants-2012_03
Patent number
US08143251B2

Reaction notes

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