Pyridinium chloride → HCID 22172761, compound

HRID 1823327Notes

Reaction equation

HRID 1823327 reaction equation
[CH2:1]([O:3][CH2:4][C:5]([NH:7][C:8]1[C:9]2[N:10]([N:20]=[N:21][N:22]=2)[C:11]([CH3:19])=[CH:12][C:13]=1[NH:14][CH2:15][CH:16]([CH3:18])[CH3:17])=O)[CH3:2].Cl.N1C=CC=CC=1>N1C=CC=CC=1>[CH2:1]([O:3][CH2:4][C:5]1[N:14]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:13]2[CH:12]=[C:11]([CH3:19])[N:10]3[N:20]=[N:21][N:22]=[C:9]3[C:8]=2[N:7]=1)[CH3:2]

Participants

4

Reactant 2

HCID 10176127Pyridinium chloride2×HCID 11666673HCID 11666673, compound

Product 1

HCID 22172761HCID 22172761, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-ethoxy-N-{7-[(2-methylpropyl)amino]-5-methyltetraazolo[1,5-a]pyridin-8-yl}acetamide (10.9 g, 35.6 mmol) and pyridine hydrochloride (10 g) in pyridine (100 mL) was heated at reflux under a nitrogen atmosphere for five days. An analysis by high-performance liquid chromatography indicated the presence of 16% starting material, and an additional 10 g of pyridine hydrochloride was added. After a total of seven days, the reaction was complete, and the solvent was removed under reduced pressure. The resulting black oil was dissolved in ethyl acetate (500 mL), and the solution was washed with water (3×200 mL), dried over magnesium sulfate, filtered, and concentrated to 200 mL. Needles began to form in the solution, which was placed in a freezer for two hours. The crystals were then filtered and washed with cold ethyl acetate to yield 6.85 g of 8-(ethoxymethyl)-7-(2-methylpropyl)-5-methyl-7H-imidazo[4,5-c]tetraazolo[1,5-a]pyridine as light brown needles, m.p. 158–160° C.

Workup

  1. temperatureat reflux under a nitrogen atmosphere for five days
  2. customAfter a total of seven days
  3. customthe solvent was removed under reduced pressure
  4. dissolutionThe resulting black oil was dissolved in ethyl acetate (500 mL)
  5. washthe solution was washed with water (3×200 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to 200 mL
  9. customto form in the solution, which
  10. filtrationThe crystals were then filtered
  11. washwashed with cold ethyl acetate

Sources & evidence

ORD record
ord-2f54a3a4401d43108841a1591087ed88
Source dataset
uspto-grants-2006_05
Patent number
US07038053B2

Reaction notes

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