Acetonitrile → HCID 57545283, compound

HRID 2383093Notes

Reaction equation

HRID 2383093 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:7]2[C:16]3[CH:15]=[CH:14][C:13]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-])=O)[CH:20]=4)=[CH:12][C:11]=3[N:10]=[C:9]([NH2:28])[C:8]=2[N:29]=1)[CH3:2].C(#N)C>[Pt].CO>[NH2:25][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][CH:22]=1)[CH2:18][O:17][C:13]1[CH:14]=[CH:15][C:16]2[C:7]3[N:6]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:5]([CH2:4][O:3][CH2:1][CH3:2])=[N:29][C:8]=3[C:9]([NH2:28])=[N:10][C:11]=2[CH:12]=1

Participants

5

Reactant 2

HCID 6342AcetonitrileHCID 67050937HCID 67050937, compound

Product 1

HCID 57545283HCID 57545283, compoundYield 9.8%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalyst3×HCID 887MethanolSolvent

Procedure

2-Ethoxymethyl-1-(2-methylpropyl)-7-(3-nitrobenzyloxy)-1H-imidazo[4,5-c]quinolin-4-amine (980 mg, 2.2 mmol), prepared as described in Example 27, was mixed with acetonitrile (30 mL), and 5% platinum on carbon (˜25 mg) was added. The reaction was placed under hydrogen pressure (50 psi, 3.4×105 Pa) overnight. An analysis by liquid chromatography/mass spectrometry (LC/MS) indicated the presence of starting material; additional 5% platinum on carbon (˜25 mg) was added. The reaction was placed under hydrogen pressure (50 psi, 3.4×105 Pa) for an additional three hours. An analysis by LC/MS again indicated that the reaction was incomplete; methanol (100 mL) and 5% platinum on carbon (200 mg) were added. The reaction was placed under hydrogen pressure (50 psi, 3.4×105 Pa) overnight. The reaction mixture was filtered through a layer of CELITE filter aid, the filter cake washed with hot methanol, and the filtrate concentrated under reduced pressure to yield a solid. The solid was purified by column chromatography on silica gel (45 g, eluting with chloroform:methanol ranging in ratios from 99:1 to 95:5) to provide two products. The first product was recrystallized from 2-propanol to provide 90 mg of 7-(3-aminobenzyloxy)-2-ethoxymethyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine as off-white crystals, mp 228.0-230.0° C.

Workup

  1. additionwas added
  2. custompressure (50 psi, 3.4×105 Pa) overnight
  3. customfor an additional three hours
  4. custompressure (50 psi, 3.4×105 Pa) overnight
  5. filtrationThe reaction mixture was filtered through a layer of CELITE
  6. filtrationfilter aid
  7. washthe filter cake washed with hot methanol
  8. concentrationthe filtrate concentrated under reduced pressure
  9. customto yield a solid
  10. customThe solid was purified by column chromatography on silica gel (45 g, eluting with chloroform:methanol ranging in ratios from 99:1 to 95:5)
  11. customto provide two products
  12. customThe first product was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-db78982be16545e1948330df21ccab58
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

Loading…