HCID 68866923, compound → HCID 54697528, compound

HRID 494112Notes

Reaction equation

HRID 494112 reaction equation
C([O:8][C:9]1[C:17]2[C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[N:14]=[C:13]([O:27][CH3:28])[C:12]=2[N:11]2[CH2:29][CH2:30][N:31]([CH3:34])[C:32](=[O:33])[C:10]=12)C1C=CC=CC=1>[OH-].[OH-].[Pd+2].CO.C(#N)C>[F:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][N:15]2[C:16](=[O:18])[C:17]3[C:9]([OH:8])=[C:10]4[C:32](=[O:33])[N:31]([CH3:34])[CH2:30][CH2:29][N:11]4[C:12]=3[C:13]([O:27][CH3:28])=[N:14]2)=[CH:21][CH:22]=1

Participants

5

Reactant 1

HCID 68866923HCID 68866923, compound

Product 1

HCID 54697528HCID 54697528, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 10-(benzyloxy)-2-(4-fluorobenzyl)-4-methoxy-8-methyl-7,8-dihydropyrazino[1′,2′:1,5]-pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione (23 mg, 0.05 mmol) and Pearlman's catalyst [23 mg, 20% Pd(OH)2 on carbon] in methanol (20 mL) was stirred under an atmosphere of hydrogen gas (1 atm) at room temperature for 25 minutes. The reaction mixture was diluted with acetonitrile and filtered. The filtrate was concentrated under vacuum, and the residue was subjected to purification on reverse phase HPLC. Collection and lyophilization of appropriate fractions provided the titled compound.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under vacuum
  3. customthe residue was subjected to purification on reverse phase HPLC
  4. customCollection and lyophilization of appropriate fractions

Sources & evidence

ORD record
ord-4dc9e447f13c4f94901ce7e75105c3c9
Source dataset
uspto-grants-2009_05
Patent number
US07538112B2

Reaction notes

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