Trifluoroacetic acid → HCID 11219222, compound

HRID 1823329Notes

Reaction equation

HRID 1823329 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:7]2[CH:12]=[C:11]([CH3:13])[N:10]3N=N[N:16]=[C:9]3[C:8]=2[N:17]=1)[CH3:2].FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>Cl.[Pt](=O)=O>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:18][CH:19]([CH3:20])[CH3:21])[C:7]2[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]([NH2:16])[C:8]=2[N:17]=1)[CH3:2]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 22172761HCID 22172761, compound

Product 1

HCID 11219222HCID 11219222, compoundYield 67.8%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 313Hydrochloric AcidSolvent

Procedure

8-(Ethoxymethyl)-7-(2-methylpropyl)-5-methyl-7H-imidazo[4,5-c]tetraazolo[1,5-a]pyridine (6.5 g, 22.5 mmol), trifluoroacetic acid (67 mL), and platinum (IV) oxide (0.47 g) are added to a stainless steel Parr vessel, which is then placed under hydrogen pressure (50 psi, 3.4×105 Pa). For the first eight hours, the vessel is flushed with hydrogen every two hours and then maintained under hydrogen pressure (50 psi, 3.4×105 Pa) overnight. The reaction mixture is filtered through a layer of CELITE filter aid, and the filter cake is washed with additional trifluoroacetic acid. The filtrate is concentrated under reduced pressure to yield a light brown oil, which is dissolved in 37% aqueous hydrochloric acid (25 mL). Sodium carbonate is added to this solution until it exhibits pH 12. The resulting solution is extracted with chloroform. The chloroform solution is dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide about 4 g of 2-(ethoxymethyl)-1-(2-methylpropyl)-6-methyl-1H-imidazo[4,5-c]pyridin-4-amine as a white solid.

Workup

  1. customFor the first eight hours, the vessel is flushed with hydrogen every two hours
  2. temperaturemaintained under hydrogen pressure (50 psi, 3.4×105 Pa) overnight
  3. filtrationThe reaction mixture is filtered through a layer of CELITE
  4. filtrationfilter aid
  5. washthe filter cake is washed with additional trifluoroacetic acid
  6. concentrationThe filtrate is concentrated under reduced pressure
  7. customto yield a light brown oil, which
  8. extractionThe resulting solution is extracted with chloroform
  9. dry with materialThe chloroform solution is dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6fffc4969bc741878dce2d14e3e2941f
Source dataset
uspto-grants-2006_05
Patent number
US07038053B2

Reaction notes

Loading…