Methyl iodide → HCID 57682578, compound

HRID 494141Notes

Reaction equation

HRID 494141 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]([NH:27][C:28](=[O:30])[CH3:29])[C:12]=2[N:11]2[CH2:31][CH2:32][N:33]([CH3:36])[C:34](=[O:35])[C:10]=12)C1C=CC=CC=1.[CH3:37][Si]([N-][Si](C)(C)C)(C)C.[Li+].IC>CN(C=O)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:34](=[O:35])[N:33]([CH3:36])[CH2:32][CH2:31][N:11]4[C:12]=3[C:13]([N:27]([CH3:37])[C:28](=[O:30])[CH3:29])=[N:14]2)=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 68863946HCID 68863946, compound

Product 1

HCID 57682578HCID 57682578, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-[10-(benzyloxy)-2-(4-fluorobenzyl)-8-methyl-1,9-dioxo-1,2,6,7,8,9-hexahydropyrazino[1′,2′:1,5]pyrrolo[2,3-d]pyridazin-4-yl]acetamide (0.13 g, 0.27 mmol) in anhydrous DMF (5 mL), a solution of lithium bis(trimethylsilyl)amide (0.4 mL, 0.4 mmol; 1 M in THF) was added. The mixture was stirred at room temperature for 10 minutes, treated with iodomethane (25 μL, 0.40 mmol), and stirred at room temperature for 1 hour. The reaction mixture was concentrated under vacuum and the residue partitioned between chloroform and dilute hydrochloric acid. The organic extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum. The title compound was debenzylated in accordance with the procedure set forth in Example 62, step 12.

Workup

  1. stirringstirred at room temperature for 1 hour
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. customthe residue partitioned between chloroform and dilute hydrochloric acid
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-cc63d14213084b2bbb85813fa89a40f4
Source dataset
uspto-grants-2009_05
Patent number
US07538112B2

Reaction notes

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