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

HRID 432704Notes

Reaction equation

HRID 432704 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]3[N:24]=[N:25][N:26]=[C:16]3[C:15]=2[NH2:27])[CH:2]=1.[C:28](OCC)(OCC)(OCC)[CH3:29].C(Cl)(Cl)Cl.CO>ClCCCl>[CH3:28][C:29]1[N:13]([CH2:12][CH2:11][O:10][CH2:9][CH2:8][CH2:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]3[N:24]=[N:25][N:26]=[C:16]3[C:15]=2[N:27]=1

Participants

5

Reactant 3

HCID 66221Triethyl orthoacetateHCID 18760199N5-[2-(3-pyridin-3-ylpropoxy)ethyl]tetrazolo[1,5-a]quinoline-4,5-diamineHCID 21584188Chloroform methanol

Product 1

HCID 187601655-methyl-6-[2-(3-pyridin-3-ylpropoxy)ethyl]-6H-imidazo[4,5-c]tetrazolo[1,5-a]quinolineYield 98.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Under an atmosphere of nitrogen, N5-[2-(3-pyridin-3-ylpropoxy)ethyl]tetrazolo[1,5-a]quinoline-4,5-diamine (0.70 g, 1.92 mmol) was dissolved in 1,2-dichloroethane (15 ml). Triethyl orthoacetate (0.53 ml, 2.88 mmol) was added via syringe and the reaction was heated to reflux for 3 hours. Analysis by thin layer chromatography (95/5 chloroform/methanol) showed complete consumption of the diamine. The reaction was quenched by the addition of water (15 ml). The phases were separated and the aqueous fraction was extracted with dichioromethane (3×10 ml). The combined organic fractions were washed with brine (15 ml), dried (Na2SO4), filtered and concentrated in vacuo to yield 0.73 g of 5-methyl-6-[2-(3-pyridin-3-ylpropoxy)ethyl]-6H-imidazo[4,5-c]tetrazolo[1,5-a]quinoline as a red oil. This material was used without further purification.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 3 hours
  3. customconsumption of the diamine
  4. customThe reaction was quenched by the addition of water (15 ml)
  5. customThe phases were separated
  6. extractionthe aqueous fraction was extracted with dichioromethane (3×10 ml)
  7. washThe combined organic fractions were washed with brine (15 ml)
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-afcc472c9197435ab6877ecff2e99128
Source dataset
uspto-grants-2003_12
Patent number
US06664260B2

Reaction notes

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