Sodium Hydroxide → HCID 58917311, compound

HRID 547322Notes

Reaction equation

HRID 547322 reaction equation
[CH3:1][C:2]1[N:3]([CH2:16][C:17]([CH3:26])([O:19][CH2:20][CH2:21][S:22]([CH3:25])(=[O:24])=[O:23])[CH3:18])[C:4]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=[C:6]([NH2:14])[C:5]=2[N:15]=1.[H][H].[OH-].[Na+]>FC(F)(F)C(O)=O.O.[Pt](=O)=O>[CH3:1][C:2]1[N:3]([CH2:16][C:17]([CH3:26])([O:19][CH2:20][CH2:21][S:22]([CH3:25])(=[O:24])=[O:23])[CH3:18])[C:4]2[C:13]3[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=3[N:7]=[C:6]([NH2:14])[C:5]=2[N:15]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 58917329HCID 58917329, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58917311HCID 58917311, compoundYield 64%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 2-methyl-1-{2-methyl-2-[2-(methylsulfonyl)ethoxy]propyl}-1H-imidazo[4,5-c]quinolin-4-amine (prepared as described in Example 21, 1.70 g, 4.52 mmol) and platinum(IV) oxide (1.0 g) in trifluoroacetic acid (23 mL) was hydrogenated on a Parr apparatus at 50 psi (3.5×105 Pa) hydrogen pressure for 20 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 (50 mL) and adjusted to pH 12 with 50% aqueous sodium hydroxide. A white solid formed that was isolated by filtration, washed with water, and recrystallized from ethanol. The crystals were isolated and dried under vacuum at 65° C. to afford 1.10 g of 2-methyl-1-{2-methyl-2-[2-(methylsulfonyl)ethoxy]propyl}-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine as white crystals, mp 226-229° 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. customA white solid formed that
  7. customwas isolated by filtration
  8. washwashed with water
  9. customrecrystallized from ethanol
  10. customThe crystals were isolated
  11. customdried under vacuum at 65° C.

Sources & evidence

ORD record
ord-2bc9aebcb0df4ac1ac4cb9ddb43fe73e
Source dataset
uspto-grants-2011_05
Patent number
US07939526B2

Reaction notes

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