Sodium Cyanide → HCID 68867663, compound

HRID 494133Notes

Reaction equation

HRID 494133 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[F:29])[CH2:5][N:6]1[C:11](=[O:12])[C:10]2[C:13]([O:22][CH3:23])=[C:14]3[C:19](=[O:20])[N:18]([CH3:21])[CH2:17][CH2:16][N:15]3[C:9]=2[C:8]([CH2:24]Cl)=[N:7]1.[C-:30]#[N:31].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[F:29])[CH2:5][N:6]1[C:11](=[O:12])[C:10]2[C:13]([O:22][CH3:23])=[C:14]3[C:19](=[O:20])[N:18]([CH3:21])[CH2:17][CH2:16][N:15]3[C:9]=2[C:8]([CH2:24][C:30]#[N:31])=[N:7]1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 68866040HCID 68866040, compound

Product 1

HCID 68867663HCID 68867663, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(3-chloro-4-fluorobenzyl)-4-(chloromethyl)-10-methoxy-8-methyl-7,8-dihydropyrazino[1′,2′:1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione (0.16 g, 0.37 mmol; Example 100) and sodium cyanide (30 mg, 0.61 mmol) in anhydrous DMF (2 mL) was heated in a sealed tube at room temperature overnight. The product mixture was concentrated under vacuum. The residue was partitioned between dichloromethane and brine. The organic extract was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with a 0 to 10% methanol in chloroform gradient. Collection and concentration of appropriate fractions afforded the title compound.

Workup

  1. concentrationThe product mixture was concentrated under vacuum
  2. customThe residue was partitioned between dichloromethane and brine
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-441b20751d834307abdbd2abf230b814
Source dataset
uspto-grants-2009_05
Patent number
US07538112B2

Reaction notes

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