HCID 58527489, compound → HCID 58527473, compound

HRID 1663438Notes

Reaction equation

HRID 1663438 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]3[CH2:18][O:17][CH2:16][C@H:15]([CH2:19][CH2:20][CH2:21][NH:22][S:23]([CH3:26])(=[O:25])=[O:24])[N:14]3[C:10]=2[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1>FC(F)(F)C(O)=O.[Pt]=O>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]3[CH2:18][O:17][CH2:16][C@H:15]([CH2:19][CH2:20][CH2:21][NH:22][S:23]([CH3:26])(=[O:25])=[O:24])[N:14]3[C:10]=2[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1

Participants

4

Reactant 1

HCID 58527489HCID 58527489, compound

Product 1

HCID 58527473HCID 58527473, compoundYield 33.6%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

N-{3-[(11S)-6-Amino-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-11-yl]propyl}methanesulfonamide (254 mg, 0.667 mmol) was dissolved in about 3 mL of trifluoroacetic acid and the solution was placed in a pressure bottle. Platinum oxide (154 mg) was then added and the reaction mixture was shaken under H2 at 50 PSI (3.4×105 Pa). After 24 hours, the reaction mixture was filtered through a pad of CELITE filter agent. The pad was rinsed with a mixture of 2-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 layer was made basic by addition of concentrated NH4OH solution until the pH was approximately 12. The layers were separated and the organic portion was washed successively with concentrated NH4OH, H2O and brine. The organic portion was dried over Na2SO4, filtered and concentrated under reduced pressure. Chromatography (SiO2, 25-33% CMA/CHCl3) gave a white solid. Crystallization from methanol/ethyl acetate gave N-{3-[(11S)-6-amino-2,3,4,8,10,11-hexahydro-1H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-11-yl]propyl}methanesulfonamide (85 mg) as white crystals, mp 197-200° 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 2-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 layer was made basic by addition of concentrated NH4OH solution until the pH was approximately 12
  8. customThe layers were separated
  9. washthe organic portion was washed successively with concentrated NH4OH, H2O and brine
  10. dry with materialThe organic portion was dried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure
  13. customChromatography (SiO2, 25-33% CMA/CHCl3) gave a white solid
  14. customCrystallization from methanol/ethyl acetate

Sources & evidence

ORD record
ord-bfbb128bab91486486e23f801913a7b2
Source dataset
uspto-grants-2011_10
Patent number
US08034938B2

Reaction notes

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