Sodium Hydroxide → HCID 58917331, compound

HRID 547318Notes

Reaction equation

HRID 547318 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:19][C:20]2([O:24][CH2:25][CH2:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH2:23][CH2:22][CH2:21]2)[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]2([O:24][CH2:25][CH2:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH2:21][CH2:22][CH2:23]2)[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 58917341HCID 58917341, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58917331HCID 58917331, compoundYield 69.1%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 2-(ethoxymethyl)-1-({1-[2-(methylsulfonyl)ethoxy]cyclobutyl}methyl)-1H-imidazo[4,5-c]quinolin-4-amine (prepared as described in Example 26, 0.500 g, 1.16 mmol) and platinum(IV) oxide (0.5 g) in trifluoroacetic acid (5 mL) was hydrogenated on a Parr apparatus at 50 psi (3.5×105 Pa) hydrogen pressure for 1 day. 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. A white solid formed that was isolated by filtration, washed with water, and recrystallized from acetonitrile. The crystals were isolated and dried under vacuum at 65° C. to afford 0.35 g of 2-(ethoxymethyl)-1-({1-[2-(methylsulfonyl)ethoxy]cyclobutyl}methyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine as a white powder, mp 186-188° 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 acetonitrile
  10. customThe crystals were isolated
  11. customdried under vacuum at 65° C.

Sources & evidence

ORD record
ord-5629d04b98164af58253436d82c8f3c5
Source dataset
uspto-grants-2011_05
Patent number
US07939526B2

Reaction notes

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