Dimethylformamide → CL-285032

HRID 1906778Notes

Reaction equation

HRID 1906778 reaction equation
[CH3:1][C:2]1[N:6]2[N:7]=[C:8]([C:11]3[CH:12]=[C:13]([NH:17][C:18](=[O:20])[CH3:19])[CH:14]=[CH:15][CH:16]=3)[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1.[CH3:21]N(C)C=O.[H-].[Na+].CI>O>[CH3:21][N:17]([C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:8]2[CH:9]=[CH:10][C:5]3[N:6]([C:2]([CH3:1])=[N:3][N:4]=3)[N:7]=2)[CH:12]=1)[C:18](=[O:20])[CH3:19]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 7532415N-(3-(3-methyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)phenyl)acetamide

Product 1

HCID 2737312CL-285032

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 12.5 g portion of N-[3-(3-methyl-1,2,4-triazolo[4,3-b]pyridazin-6-yl)phenyl]acetamide was added to 500 ml of dimethylformamide under argon. A 2.47 g portion of sodium hydride (50% in oil) was added, this mixture was stirred one hour, then 3.2 ml of methyl iodide was added. This mixture was stirred for 2.5 days, then poured into 1.5 liters of water and extracted with 150 ml portions of dichloromethane. The extracts were combined, dried and concentrated in vacuo. The residue was chromatographed as described in Example 1. Fractions 8-15 were combined, concentrated and the solid recrystallized from dichloromethane-hexane, giving 8.5 g of the desired product, mp 200°-203° C.

Workup

  1. stirringThis mixture was stirred for 2.5 days
  2. extractionextracted with 150 ml portions of dichloromethane
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed
  6. concentrationconcentrated
  7. customthe solid recrystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-249bd32319224e69b8819f0e3692e035
Source dataset
uspto-grants-1987_03
Patent number
US04654343

Reaction notes

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