Sodium Hydroxide → HCID 58917317, compound

HRID 547297Notes

Reaction equation

HRID 547297 reaction equation
[CH3:1][S:2]([CH2:5][CH2:6][O:7][CH2:8][CH2:9][N:10]1[C:22]2[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]=[C:14]([NH2:23])[C:13]=2[N:12]=[C:11]1[CH3:24])(=[O:4])=[O:3].[H][H].[OH-].[Na+]>FC(F)(F)C(O)=O.O.[Pt]=O>[CH3:1][S:2]([CH2:5][CH2:6][O:7][CH2:8][CH2:9][N:10]1[C:22]2[C:21]3[CH2:20][CH2:19][CH2:18][CH2:17][C:16]=3[N:15]=[C:14]([NH2:23])[C:13]=2[N:12]=[C:11]1[CH3:24])(=[O:3])=[O:4]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 11772417HCID 11772417, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 58917317HCID 58917317, compoundYield 76.4%

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Solid platinum oxide (0.5) was added to a solution of 1-{2-[2-(methylsulfonyl)ethoxy]ethyl}-2-methyl-1H-imidazo[4,5-c]quinolin-4-amine (0.9 g, 2.6 mmol) in trifluoroacetic acid (7 mL) in a Parr vessel. The vessel was placed on a shaker and then pressurized with hydrogen to 50 psi (3.4×105 Pa). Hydrogen was added periodically to maintain the pressure. After 55 hours the reaction mixture was purged with nitrogen and then filtered through a layer of CELITE filter agent. The filter cake was washed with dichloromethane (˜200 mL). The filtrate was concentrated under reduced pressure to provide an oil. The oil was dissolved in water (50 mL). The pH of the solution was adjusted to pH 12 by the addition of aqueous 50% sodium hydroxide and then the solution was extracted with dichloromethane (2×100 mL). The combined extracts were washed with brine (100 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to provide crude product as a white foam. This material was recrystallized from ethyl acetate. The resulting off white plates were isolated by filtration, washed with ethyl acetate and dried under vacuum at 65° C. for 4 hours to provide 0.7 g of 1-{2-[2-(methylsulfonyl)ethoxy]ethyl}-2-methyl-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine, mp 173-175° C. 1H NMR (300 MHz, DMSO-d6) δ 5.65 (bs, 2H), 4.40 (t, J=5.0 Hz, 2H), 3.73 (t, J=5.6 Hz, 2H), 3.32 (t, J=5.6 Hz, 2H), 2.91 (m, 2H), 2.78 (s, 3H) 2.65 (m, 2H), 2.47 (s, 3H), 1.75 (m, 4H); MS (APCI) m/z 353 (M+

Workup

  1. temperatureto maintain the pressure
  2. customAfter 55 hours the reaction mixture was purged with nitrogen
  3. filtrationfiltered through a layer of CELITE filter agent
  4. washThe filter cake was washed with dichloromethane (˜200 mL)
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customto provide an oil
  7. extractionthe solution was extracted with dichloromethane (2×100 mL)
  8. washThe combined extracts were washed with brine (100 mL)
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customto provide crude product as a white foam
  13. customThis material was recrystallized from ethyl acetate
  14. customThe resulting off white plates were isolated by filtration
  15. washwashed with ethyl acetate
  16. customdried under vacuum at 65° C. for 4 hours

Sources & evidence

ORD record
ord-7a25a3e6e39d4917b21e82fcd14ea3fa
Source dataset
uspto-grants-2011_05
Patent number
US07939526B2

Reaction notes

Loading…