Sodium Hydroxide → HCID 58917328, compound

HRID 547319Notes

Reaction equation

HRID 547319 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:19][C:20]([CH3:29])([O:22][CH2:23][CH2:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH3:21])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:17])[C:8]=2[N:18]=1)[CH3:2].[H][H].[OH-].[Na+]>FC(F)(F)C(O)=O.O.[Pt](=O)=O>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:19][C:20]([CH3:21])([O:22][CH2:23][CH2:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH3:29])[C:7]2[C:16]3[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=3[N:10]=[C:9]([NH2:17])[C:8]=2[N:18]=1)[CH3:2]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 58917332HCID 58917332, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58917328HCID 58917328, compoundYield 75.8%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 2-(ethoxymethyl)-1-{2-methyl-2-[2-(methylsulfonyl)ethoxy]propyl}-1H-imidazo[4,5-c]quinolin-4-amine (prepared as described in Example 9, 1.70 g, 4.04 mmol) and platinum(IV) oxide (1.0 g) in trifluoroacetic acid (20 mL) was hydrogenated on a Parr apparatus at 50 psi (3.5×105 Pa) hydrogen pressure for 40 hours. The mixture was filtered through CELITE filter agent, which was washed afterwards with dichloromethane. The filtrate was concentrated under reduced pressure to afford an oil that was suspended in water (20 mL) and adjusted to pH 13 with 50% aqueous sodium hydroxide. The mixture was extracted with dichloromethane (3×50 mL). The organic layers were combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure to yield a white solid. The solid was recrystallized from toluene to afford 1.3 g of 2-(ethoxymethyl)-1-{2-methyl-2-[2-(methylsulfonyl)ethoxy]propyl}-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine as a white, fluffy powder, mp 150-153° C.

Workup

  1. filtrationThe mixture was filtered through CELITE
  2. filtrationfilter agent, which
  3. washwas washed afterwards with dichloromethane
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto afford an oil that
  6. extractionThe mixture was extracted with dichloromethane (3×50 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto yield a white solid
  11. customThe solid was recrystallized from toluene

Sources & evidence

ORD record
ord-9ab5184ebcb74242b036a2fdfca2262a
Source dataset
uspto-grants-2011_05
Patent number
US07939526B2

Reaction notes

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