1,1,1-Trimethoxybutane → ethyl 4-(5,6-dimethyl-8-propyl-7H-imidazo[4,5-c]tetraazolo[1,5-a]pyridin-7-yl)butanoate

HRID 2366703Notes

Reaction equation

HRID 2366703 reaction equation
Cl.N1C=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC)(OC)(OC)CCC.[NH2:18][C:19]1[C:20]2[N:21]([N:36]=[N:37][N:38]=2)[C:22]([CH3:35])=[C:23]([CH3:34])[C:24]=1[NH:25][CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30]>C1(C)C=CC=CC=1>[CH3:35][C:22]1[N:21]2[N:36]=[N:37][N:38]=[C:20]2[C:19]2[N:18]=[C:3]([CH2:4][CH2:5][CH3:6])[N:25]([CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:24]=2[C:23]=1[CH3:34]

Participants

5

Reactant 3

HCID 1235121,1,1-TrimethoxybutaneHCID 10176127Pyridinium chlorideHCID 57447079Ethyl 4-[(8-amino-5,6-dimethyltetraazolo[1,5-a]pyridin-7-yl)amino]butanoate

Product 1

HCID 69506777ethyl 4-(5,6-dimethyl-8-propyl-7H-imidazo[4,5-c]tetraazolo[1,5-a]pyridin-7-yl)butanoateYield 150.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

For Examples 40 and 41, pyridine hydrochloride (1.34 g, 11.6 mmol) and trimethyl orthobutyrate (5.42 mL, 34.1 mmol) were sequentially added with stirring to a solution of ethyl 4-[(8-amino-5,6-dimethyltetraazolo[1,5-a]pyridin-7-yl)amino]butanoate (9.1 g, 31 mmol) in toluene (310 mL) under a nitrogen atmosphere. The reaction was heated at reflux for 1.5 hours, allowed to cool to ambient temperature overnight, and concentrated under reduced pressure. The residue was partitioned between chloroform (300 mL) and saturated aqueous sodium bicarbonate (75 mL). The aqueous layer was extracted with chloroform (2×100 mL), and the combined organic fractions were washed with saturated aqueous sodium bicarbonate (2×75 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting solid was triturated with ethyl acetate and isolated by filtration to provide 6.0 g of ethyl 4-(5,6-dimethyl-8-propyl-7H-imidazo[4,5-c]tetraazolo[1,5-a]pyridin-7-yl)butanoate as a white solid.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 1.5 hours
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was partitioned between chloroform (300 mL) and saturated aqueous sodium bicarbonate (75 mL)
  5. extractionThe aqueous layer was extracted with chloroform (2×100 mL)
  6. washthe combined organic fractions were washed with saturated aqueous sodium bicarbonate (2×75 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe resulting solid was triturated with ethyl acetate
  11. customisolated by filtration

Sources & evidence

ORD record
ord-ee442391adbd4cc0ab6dcb9db7351fbe
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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