Chloroform → HCID 11654553, compound

HRID 1663439Notes

Reaction equation

HRID 1663439 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][C:23]([N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)=[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.[NH4+].[OH-].C(Cl)(Cl)Cl>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][C:23]([N:25]4[CH2:26][CH2:27][O:28][CH2:29][CH2:30]4)=[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

6

Reactant 3

HCID 6212ChloroformHCID 14923Ammonium HydroxideHCID 58527496HCID 58527496, compound

Product 1

HCID 11654553HCID 11654553, compoundYield 56.1%

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}morpholine-4-carboxamide (698 mg, 1.70 mmol) was dissolved in 5 mL of trifluoroacetic acid and the solution was placed in a pressure bottle. Platinum oxide (386 mg) was then added and the reaction mixture was shaken under H2 at 50 PSI (3.4×105 Pa). After 2 days, the reaction mixture was filtered through a pad of CELITE filter agent. The pad was rinsed with a mixture of methanol and CH2Cl2 and the combined filtrates were concentrated under reduced pressure to give a syrup. The syrup was portioned between 20 mL of concentrated NH4OH solution and 50 mL of CHCl3. The layers were separated and the aqueous portion was extracted with an additional 50 mL of CHCl3. The combined organic portions were washed successively with concentrated NH4OH, H2O and brine. The organic portion was dried over Na2SO4, filtered and concentrated under reduced pressure. Chromatography (SiO2, 20% CMA/CHCl3) gave a fluffy, white solid. Crystallization from methanol/propyl 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}morpholine-4-carboxamide (395 mg) as fluffy, white needles, mp 154-156° 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 methanol and CH2Cl2
  4. concentrationthe combined filtrates were concentrated under reduced pressure
  5. customto give a syrup
  6. customThe layers were separated
  7. extractionthe aqueous portion was extracted with an additional 50 mL of CHCl3
  8. washThe combined organic portions were washed successively with concentrated NH4OH, H2O and brine
  9. dry with materialThe organic portion was dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customChromatography (SiO2, 20% CMA/CHCl3) gave a fluffy, white solid
  13. customCrystallization from methanol/propyl acetate

Sources & evidence

ORD record
ord-ff6dd37200cb4d03a4fa44b58c411047
Source dataset
uspto-grants-2011_10
Patent number
US08034938B2

Reaction notes

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