Hydrochloric Acid → HCID 67435233, compound

HRID 1663447Notes

Reaction equation

HRID 1663447 reaction equation
O.[ClH:2].Cl.[NH2:4][CH2:5][CH2:6][CH2:7][C@@H:8]1[N:13]2[C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17]=[C:16]([NH2:24])[C:15]=3[N:25]=[C:12]2[CH2:11][N:10]([S:26]([CH3:29])(=[O:28])=[O:27])[CH2:9]1.Cl>FC(F)(F)C(O)=O.C(O)C.[Pt]=O>[OH2:27].[ClH:2].[ClH:2].[NH2:4][CH2:5][CH2:6][CH2:7][C@@H:8]1[N:13]2[C:14]3[C:23]4[CH2:22][CH2:21][CH2:20][CH2:19][C:18]=4[N:17]=[C:16]([NH2:24])[C:15]=3[N:25]=[C:12]2[CH2:11][N:10]([S:26]([CH3:29])(=[O:27])=[O:28])[CH2:9]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 67434271HCID 67434271, compound

Product 1

HCID 67435233HCID 67435233, compoundYield 121.7%

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

(11S)-11-(3-Aminopropyl)-9-(methylsulfonyl)-8,9,10,11-tetrahydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinolin-6-amine dihydrochloride hydrate (1.30 g, 2.80 mmol) was dissolved in 10 mL of trifluoroacetic acid and the solution was placed in a pressure bottle. Platinum oxide (635 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 ethanol and the combined filtrates were concentrated under reduced pressure. The resulting residue was concentrated with 2 N HCl in ethanol three times to give white solid. The white solid was treated with hot 2 N HCl in ethanol and the solution was allowed to cool, leaving a white solid. The solid was isolated by filtration and rinsed with ethanol and dried under vacuum at 80° C. to give (11S)-11-(3-aminopropyl)-9-(methylsulfonyl)-1,2,3,4,8,9,10,11-octahydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinolin-6-amine dihydrochloride hydrate (800 mg) as an off-white powder.

Workup

  1. filtrationthe reaction mixture was filtered through a pad of CELITE
  2. filtrationfilter agent
  3. washThe pad was rinsed with ethanol
  4. concentrationthe combined filtrates were concentrated under reduced pressure
  5. concentrationThe resulting residue was concentrated with 2 N HCl in ethanol three times
  6. customto give white solid
  7. temperatureto cool
  8. customleaving a white solid
  9. customThe solid was isolated by filtration
  10. washrinsed with ethanol
  11. customdried under vacuum at 80° C.

Sources & evidence

ORD record
ord-9b9768b4c17b468a8cb1c53b15379072
Source dataset
uspto-grants-2011_10
Patent number
US08034938B2

Reaction notes

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