Hydrochloric Acid → HCID 58406157, compound

HRID 549156Notes

Reaction equation

HRID 549156 reaction equation
C([O:8][C@H:9]([C@@H:11]1[N:16]2[C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]=[C:19]([NH2:27])[C:18]=3[N:28]=[C:15]2[CH2:14][O:13][CH2:12]1)[CH3:10])C1C=CC=CC=1.Cl>CO.[Pd].C(O)C>[NH2:27][C:19]1[C:18]2[N:28]=[C:15]3[CH2:14][O:13][CH2:12][C@H:11]([C@@H:9]([OH:8])[CH3:10])[N:16]3[C:17]=2[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 58406183HCID 58406183, compound

Product 1

HCID 58406157HCID 58406157, compoundYield 32.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

(11R)-11-[(1S)-1-(Benzyloxy)ethyl]-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-6-amine (512 mg, 1.37 mmol) was dissolved in 30 mL of methanol and the solution was placed in a pressure bottle. Palladium on carbon (10%, 200 mg) and 2.5 mL of 3 M HCl in ethanol were 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 methanol and the combined filtrates were concentrated under reduced pressure. The residue was dissolved in H2O and the solution was made basic by the addition of concentrated aqueous NH4OH solution. The aqueous solution was extracted with 10% MeOH/CHCl3 several times and the combined organic layers were concentrated under reduced pressure. Chromatography (SiO2, 25-75% CMA/CHCl3) gave an off-white powder. Crystallization from ethyl acetate and methanol gave 125 mg of the desired compound as a white, fluffy solid, mp 207.6-208.7° C.

Workup

  1. filtrationthe reaction mixture was filtered through a pad of CELITE
  2. filtrationfilter agent
  3. washThe pad was rinsed with methanol
  4. concentrationthe combined filtrates were concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in H2O
  6. additionthe solution was made basic by the addition of concentrated aqueous NH4OH solution
  7. extractionThe aqueous solution was extracted with 10% MeOH/CHCl3 several times
  8. concentrationthe combined organic layers were concentrated under reduced pressure
  9. customChromatography (SiO2, 25-75% CMA/CHCl3) gave an off-white powder
  10. customCrystallization from ethyl acetate and methanol

Sources & evidence

ORD record
ord-8a742f637aa347f7a3ff421a93d65a54
Source dataset
uspto-grants-2011_05
Patent number
US07943609B2

Reaction notes

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