2,3-Diaminopyridine → HCID 22711785, compound

HRID 349206Notes

Reaction equation

HRID 349206 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[C:2]=1[NH2:8].Cl.C(O[C:13](=N)[CH2:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:17][CH2:16]1)C>CO>[NH:7]1[C:3]2[C:2](=[N:1][CH:6]=[CH:5][CH:4]=2)[N:8]=[C:13]1[CH2:14][CH:15]1[CH2:16][CH2:17][N:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:19][CH2:20]1

Participants

4

Reactant 2

HCID 99562,3-DiaminopyridineHCID 22711787HCID 22711787, compound

Product 1

HCID 22711785HCID 22711785, compoundYield 52.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2,3-pyridinediamine (0.05 mol) and ethyl 4-(2-ethoxy-2-iminoethyl)-1-piperidinecarboxylate monohydrochloride (0.05 mol) in methanol (150 ml) was stirred and refluxed for 3 days. The solvent was evaporated and the residue was taken up in CH2Cl2. The organic solution was washed with K2CO3 10%, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 94/6/0.1). The pure fractions were collected and the solvent was evaporated, yielding 7.6 g of ethyl 4-[(1H-imidazo[4,5-b]pyridin-2-yl)methyl]-1-piperidinecarboxylate (52%) (interm. 9).

Workup

  1. temperaturerefluxed for 3 days
  2. customThe solvent was evaporated
  3. washThe organic solution was washed with K2CO3 10%
  4. customdried
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 94/6/0.1)
  8. customThe pure fractions were collected
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-7128e42717704431a20e3ae8b27f458a
Source dataset
uspto-grants-2007_02
Patent number
US07179811B2

Reaction notes

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