Methanol → HCID 68866923, compound

HRID 494111Notes

Reaction equation

HRID 494111 reaction equation
[CH2:1]([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)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:35]Cl.CO.C[Si](C=[N+]=[N-])(C)C>CCCCCC.C(O)(=O)C>[CH2:1]([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][CH3:35])[C:12]=2[N:11]2[CH2:28][CH2:29][N:30]([CH3:33])[C:31](=[O:32])[C:10]=12)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 167693TrimethylsilyldiazomethaneHCID 178480574HCID 178480574, compound

Product 1

HCID 68866923HCID 68866923, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 8058HexaneSolvent

Procedure

A suspension 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 (0.50 g, 1.11 mmol) in mixture of dichloromethane (20 mL) and methanol (1 mL) at room temperature was treated with a solution of (trimethylsilyl)diazomethane in hexane. After stirring for 30 minutes, the resultant homogeneous solution was treated with a few drops of acetic acid, and the mixture was concentrated under vacuum. The residue was partitioned between chloroform and brine. The organic extract was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was subject to column chromatography on silica gel eluting with 2% methanol in chloroform. Collection and concentration of the faster eluting major product provide the titled compound.

Workup

  1. concentrationthe mixture was concentrated under vacuum
  2. customThe residue was partitioned between chloroform and brine
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customCollection and concentration of the
  8. washfaster eluting major product

Sources & evidence

ORD record
ord-ebd0d61a48444e118c077eeda45c5e65
Source dataset
uspto-grants-2009_05
Patent number
US07538112B2

Reaction notes

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