Hydrochloric Acid → HCID 58406179, compound

HRID 221585Notes

Reaction equation

HRID 221585 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 58406161HCID 58406161, compound

Product 1

HCID 58406179HCID 58406179, compoundYield 90.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

(11R)-11-[(1R)-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, 25-50% CMA/CHCl3) gave an off-white powder. Crystallization from ethyl acetate and methanol gave 353 mg of the title compound as white needles, mp 215.3-218.6° 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, 25-50% CMA/CHCl3) gave an off-white powder
  10. customCrystallization from ethyl acetate and methanol

Sources & evidence

ORD record
ord-cb24f4c02f7d4100bc6d5c12565a7539
Source dataset
uspto-grants-2012_06
Patent number
US08207162B2

Reaction notes

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