Dimethylformamide → N-Ethyl-N-[3-(3-methyl-1,2,4-triazolo[4,3-b]pyridazin-6-yl)phenyl]cyclopropanecarboxamide

HRID 1906804Notes

Reaction equation

HRID 1906804 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]([CH:20]4[CH2:22][CH2:21]4)=[O:19])[CH:14]=[CH:15][CH:16]=3)[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1.[H-].[Na+].CN(C)C=O.[CH2:30](I)[CH3:31]>O>[CH2:30]([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]([CH:20]1[CH2:22][CH2:21]1)=[O:19])[CH3:31]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 7532445N-(3-{3-methyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl}phenyl)cyclopropanecarboxamide

Product 1

HCID 15595673N-Ethyl-N-[3-(3-methyl-1,2,4-triazolo[4,3-b]pyridazin-6-yl)phenyl]cyclopropanecarboxamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture 1.57 g of N-[3-(3-methyl-1,2,4-triazolo[4,3-b]pyridazin-6-yl)phenyl]cyclopropanecarboxamide, 0.36 g of sodium hydride (50% in oil) and 200 ml of dry dimethylformamide under argon was stirred at room temperature for 1 hour and then 0.60 ml of ethyl iodide was added. After stirring overnight, the mixture was poured into 200 ml of water and extracted with dichloromethane. The combined extracts were dried, the solvent removed and the residue chromatographed on a silica gel column with dichlormethane-methanol (97:3) as solvent. The fractions containing product were combined, the solvent removed and the solid recrystallized from dichloromethane-hexane to give 0.80 g of pale yellow crystals, mp 149°-151° C.

Workup

  1. extractionextracted with dichloromethane
  2. customThe combined extracts were dried
  3. customthe solvent removed
  4. customthe residue chromatographed on a silica gel column with dichlormethane-methanol (97:3) as solvent
  5. additionThe fractions containing product
  6. customthe solvent removed
  7. customthe solid recrystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-a987f4f175464510a6ac60263a3415c3
Source dataset
uspto-grants-1987_03
Patent number
US04654343

Reaction notes

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