Sodium Hydroxide → HCID 11708881, compound

HRID 1373985Notes

Reaction equation

HRID 1373985 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:19][OH:20])[N:14]([NH:15][CH:16]([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[OH-].[Na+]>FC(F)(F)C(O)=O.C(Cl)(Cl)Cl.O.[Pt](=O)=O>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:19][OH:20])[N:14]([NH:15][CH:16]([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1

Participants

7

Reactant 2

HCID 14798Sodium HydroxideHCID 11601484HCID 11601484, compound

Product 1

HCID 11708881HCID 11708881, compound

Reagents, catalysts & solvents 4

HCID 345198Adams' catalystCatalystHCID 962WaterSolventHCID 6212ChloroformSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of [4-amino-1-(isopropylamino)-1H-imidazo[4,5-c]quinolin-2-yl]methanol (0.120 g, 0.442 mmol) and platinum (IV) oxide (0.100 g, 0.422 mmol) in trifloroacetic acid (10 mL) was hydrogenated on a Parr apparatus at 50 psi (3.4×105 Pa) at room temperature for 18 hours. The mixture was diluted with chloroform (20 mL) and filtered through a pad of CELITE filter agent. The filter agent was rinsed with a 4:1 chloroform/methanol solution. The filtrate was concentrated under reduced pressure to yield an oil that was suspended in water (10 mL) and treated with 10% aqueous sodium hydroxide until pH 7 was reached. A white precipitate was isolated by filtration, rinsed with water, and dried overnight under vacuum to provide [4-amino-1-(isopropylamino)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-2-yl]methanol.

Workup

  1. filtrationfiltered through a pad of CELITE
  2. filtrationfilter agent
  3. washThe filter agent was rinsed with a 4:1 chloroform/methanol solution
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto yield an oil that
  6. customA white precipitate was isolated by filtration
  7. washrinsed with water
  8. customdried overnight under vacuum

Sources & evidence

ORD record
ord-86ae41a6a1f9444fbbcc7c93268d8f08
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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