(11S)-11-isopropyl-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-6-amine → (11S)-11-Isopropyl-2,3,4,8,10,11-hexahydro-1H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-6-amine

HRID 549099Notes

Reaction equation

HRID 549099 reaction equation
[CH:1]([C@@H:4]1[N:9]2[C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[N:13]=[C:12]([NH2:20])[C:11]=3[N:21]=[C:8]2[CH2:7][O:6][CH2:5]1)([CH3:3])[CH3:2]>FC(F)(F)C(O)=O.[Pt]=O>[CH:1]([C@@H:4]1[N:9]2[C:10]3[C:19]4[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=4[N:13]=[C:12]([NH2:20])[C:11]=3[N:21]=[C:8]2[CH2:7][O:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 11565409(11S)-11-isopropyl-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-6-amine

Product 1

HCID 58406153(11S)-11-Isopropyl-2,3,4,8,10,11-hexahydro-1H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-6-amineYield 66.4%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

(11S)-11-Isopropyl-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-6-amine (320 mg, 1.13 mmol) was dissolved in 3 mL of trifluoroacetic acid and the solution was placed in a pressure bottle. Platinum oxide (250 mg) was then added and the reaction mixture was shaken under H2 at 50 PSI (3.4×105 Pa). After 20 hours, the reaction mixture was filtered through a pad of CELITE filter agent. The pad was rinsed with a mixture of iso-propanol and CH2Cl2 and the combined filtrates were concentrated under reduced pressure to give a syrup. The syrup was partitioned between H2O and CHCl3. The aqueous portion was made basic by addition of 10% NaOH solution until pH >12. The layers were separated and the organic portion was washed successively with 10% NaOH (2×), H2O and brine. The organic portion was then dried over Na2SO4, filtered and concentrated under reduced pressure to give a tan foam. Crystallization from ethyl acetate gave the title compound (215 mg) as light amber crystals, mp 158.0-160.0° C.

Workup

  1. filtrationthe reaction mixture was filtered through a pad of CELITE
  2. filtrationfilter agent
  3. washThe pad was rinsed with a mixture of iso-propanol and CH2Cl2
  4. concentrationthe combined filtrates were concentrated under reduced pressure
  5. customto give a syrup
  6. customThe syrup was partitioned between H2O and CHCl3
  7. additionThe aqueous portion was made basic by addition of 10% NaOH solution until pH >12
  8. customThe layers were separated
  9. washthe organic portion was washed successively with 10% NaOH (2×), H2O and brine
  10. dry with materialThe organic portion was then dried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure
  13. customto give a tan foam
  14. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-6b58755d358b4405af834bffe1c2e94e
Source dataset
uspto-grants-2011_05
Patent number
US07943609B2

Reaction notes

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