HCID 58923890, compound → HCID 136353475, compound

HRID 1364076Notes

Reaction equation

HRID 1364076 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]3[N:22]4[CH2:23][CH2:24][N:25]([S:27]([CH3:30])(=[O:29])=[O:28])[CH2:26][C:21]4=[N:20][C:14]=3[C:15]([NH2:19])=[N:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.ClCCl.[Pd]>[NH2:19][C:15]1[C:14]2[N:20]=[C:21]3[CH2:26][N:25]([S:27]([CH3:30])(=[O:29])=[O:28])[CH2:24][CH2:23][N:22]3[C:13]=2[C:12]2[C:17](=[CH:18][C:9]([OH:8])=[CH:10][CH:11]=2)[N:16]=1

Participants

5

Reactant 1

HCID 58923890HCID 58923890, compound

Product 1

HCID 136353475HCID 136353475, compoundYield 35.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

3-(Benzyloxy)-9-(methylsulfonyl)-8,9,10,11-tetrahydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinolin-6-amine, (3.34 g, 10.0 mmol) prepared as described in Example 368, was dissolved in a mixture of methanol (100 mL) and dichloromethane (100 mL) and transferred to a hydrogenation vessel charged with 10% palladium on carbon (5 g, 47 mmol). The vessel was placed under hydrogen pressure (50 psi, 3.45×105 Pa) and shaken for two days at ambient temperature. An analysis by LC/MS indicated the presence of starting material. The catalyst was removed by filtration through a layer of CELITE filter aid, and the filtrate was placed under hydrogen pressure (50 psi, 3.45×105 Pa) again for two days in the presence of 10% palladium on carbon (5 g, 47 mmol). The catalyst was removed by filtration through a layer of CELITE filter aid, and the filtrate was concentrated under reduced pressure. The residue (560 mg) was combined with material from another run to provide 1.19 g of 6-amino-9-(methylsulfonyl)-8,9,10,11-tetrahydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinolin-3-ol.

Workup

  1. customtransferred to a hydrogenation vessel
  2. customThe catalyst was removed by filtration through a layer of CELITE
  3. filtrationfilter aid
  4. customagain for two days
  5. customThe catalyst was removed by filtration through a layer of CELITE
  6. filtrationfilter aid
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-60d4c75441094280a63337f385ccbf99
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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