Ethyl orthoformate → 6-[2-(3-pyridin-3-ylpropoxy)ethyl]-6H-imidazo[4,5-c]tetrazolo[1,5-a]quinoline

HRID 432702Notes

Reaction equation

HRID 432702 reaction equation
[CH:1](OCC)(OCC)OCC.[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][NH:23][C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]3[N:34]=[N:35][N:36]=[C:26]3[C:25]=2[NH2:37])[CH:12]=1>ClCCCl.C(=O)(O)[O-].[Na+]>[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][N:23]2[C:24]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[N:27]4[N:34]=[N:35][N:36]=[C:26]4[C:25]=3[N:37]=[CH:1]2)[CH:12]=1

Participants

5

Reactant 2

HCID 31214Ethyl orthoformateHCID 18760199N5-[2-(3-pyridin-3-ylpropoxy)ethyl]tetrazolo[1,5-a]quinoline-4,5-diamine

Product 1

HCID 187601846-[2-(3-pyridin-3-ylpropoxy)ethyl]-6H-imidazo[4,5-c]tetrazolo[1,5-a]quinolineYield 90.7%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Triethyl orthoformate (21.1 ml, 127 mmol) was added to a solution of N5-[2-(3-pyridin-3-ylpropoxy)ethyl]tetrazolo[1,5-a]quinoline-4,5-diamine (30.8 g, 84.7 mmol) in 1,2-dichloroethane (750 ml) and the reaction was heated to reflux for 3 hours. The reaction was cooled to room temperature and diluted with saturated sodium bicarbonate (200 ml). The phases were separated and the aqueous layer was extracted with dichloromethane (3×75 ml). The combined organic fractions were washed with brine (200 ml), dried (Na2SO4) and concentrated to provide an orange solid. The solid was triturated with diethyl ether and then filtered to yield 28.7 g of 6-[2-(3-pyridin-3-ylpropoxy)ethyl]-6H-imidazo[4,5-c]tetrazolo[1,5-a]quinoline as a tan/orange solid.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 3 hours
  3. customThe phases were separated
  4. extractionthe aqueous layer was extracted with dichloromethane (3×75 ml)
  5. washThe combined organic fractions were washed with brine (200 ml)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customto provide an orange solid
  9. customThe solid was triturated with diethyl ether
  10. filtrationfiltered

Sources & evidence

ORD record
ord-0f0e109acde2476cbde5846b8ca307b1
Source dataset
uspto-grants-2003_12
Patent number
US06664260B2

Reaction notes

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