HCID 178480574, compound → HCID 178480572, compound

HRID 494110Notes

Reaction equation

HRID 494110 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]([OH:27])[C:12]=2[N:11]2[CH2:28][CH2:29][N:30]([CH3:33])[C:31](=[O:32])[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:31](=[O:32])[N:30]([CH3:33])[CH2:29][CH2:28][N:11]4[C:12]=3[C:13]([OH:27])=[N:14]2)=[CH:21][CH:22]=1

Participants

5

Reactant 1

HCID 178480574HCID 178480574, compound

Product 1

HCID 178480572HCID 178480572, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 10-(benzyloxy)-2-(4-fluorobenzyl)-4-hydroxy-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 [25 mg, 20% Pd(OH)2 on carbon] in methanol (10 mL) was stirred under an atmosphere of hydrogen gas (1 atm) at room temperature for 45 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-89cc3a69cffd4c37a9c99a143c4ae237
Source dataset
uspto-grants-2009_05
Patent number
US07538112B2

Reaction notes

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