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

HRID 329631Notes

Reaction equation

HRID 329631 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 dichloromethane-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 dichloromethane-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-391f9344529f49489fdd1fa8af85cdbf
Source dataset
uspto-grants-1990_01
Patent number
US04892873

Reaction notes

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