HCID 16226437, compound → HCID 57717551, compound

HRID 1360490Notes

Reaction equation

HRID 1360490 reaction equation
[CH2:1]([N:5]1[C:17]([CH2:18][CH2:19][S:20]([CH2:23][CH2:24][CH3:25])(=[O:22])=[O:21])=[C:16]2[C:7]([C:8]([NH2:26])=[N:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=32)=[N:6]1)[CH2:2][CH2:3][CH3:4]>FC(F)(F)C(O)=O.[Pt](=O)=O>[CH2:1]([N:5]1[C:17]([CH2:18][CH2:19][S:20]([CH2:23][CH2:24][CH3:25])(=[O:21])=[O:22])=[C:16]2[C:7]([C:8]([NH2:26])=[N:9][C:10]3[CH2:11][CH2:12][CH2:13][CH2:14][C:15]=32)=[N:6]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 16226437HCID 16226437, compound

Product 1

HCID 57717551HCID 57717551, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 2-butyl-1-[2-(propylsulfonyl)ethyl]-2H-pyrazolo[3,4-c]quinolin-4-amine (prepared as described in Example 60, 0.50 g, 1.3 mmol) in trifluoroacetic acid (6 mL) was treated with platinum (IV) oxide (0.5 g) and shaken under hydrogen pressure (50 psi, 3.4×105 Pa) for 20 hours on a Parr apparatus. The reaction mixture was filtered through a layer of CELITE filter agent, and the CELITE filter agent was rinsed with dichloromethane (100 mL) until the rinses were clear. The filtrate was concentrated under reduced pressure. The oil was suspended in water (20 mL) and treated with 50% aqueous sodium hydroxide to adjust the mixture to pH 14, causing a precipitate to form. The mixture was stirred for 1 hour, then the precipitate was isolated by filtration and washed with water. The white powder was recrystallized from acetonitrile (5 mL). The crystals were isolated by filtration, washed with acetonitrile, and dried under vacuum at 65° C. to afford 0.40 g of 2-butyl-1-[2-(propylsulfonyl)ethyl]-6,7,8,9-tetrahydro-2H-pyrazolo[3,4-c]quinolin-4-amine as white crystals, mp 173-175° C.

Workup

  1. filtrationThe reaction mixture was filtered through a layer of CELITE filter agent
  2. filtrationthe CELITE filter agent
  3. washwas rinsed with dichloromethane (100 mL) until the rinses
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. additiontreated with 50% aqueous sodium hydroxide
  6. customto form
  7. stirringThe mixture was stirred for 1 hour
  8. customthe precipitate was isolated by filtration
  9. washwashed with water
  10. customThe white powder was recrystallized from acetonitrile (5 mL)
  11. customThe crystals were isolated by filtration
  12. washwashed with acetonitrile
  13. customdried under vacuum at 65° C.

Sources & evidence

ORD record
ord-3b6afc5e40d549e4904d0992c0ee9318
Source dataset
uspto-grants-2011_02
Patent number
US07879849B2

Reaction notes

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