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

HRID 1906780Notes

Reaction equation

HRID 1906780 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:21])[CH2:19][CH3:20])[CH:14]=[CH:15][CH:16]=3)[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1.[H-].[Na+].[CH2:24](I)[CH3:25]>CN(C)C=O>[CH2:24]([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:21])[CH2:19][CH3:20])[CH3:25]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 7532416N-(3-(3-methyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)phenyl)propionamide

Product 1

HCID 15595647N-Ethyl-N-[3-(3-methyl-1,2,4-triazolo[4,3-b]pyridazin-6-yl)phenyl]propanamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 6.1 g of N-[3-(3-methyl-1,2,4-triazolo[4,3-b]pyridazin-6-yl)phenyl]propanamide in 200 ml of dry dimethylformamide under argon, was added 1.1 g of sodium hydride (50% in oil). The mixture was stirred for one hour, then 1.86 ml of ethyl iodide was added. This mixture was stirred overnight and then treated as described in Example 1. The chromatography fractions containing the product were combined and the solid recrystallized as described in Example 1, giving 4.37 g of the desired product, mp 145°-148° C.

Workup

  1. stirringThis mixture was stirred overnight
  2. additiontreated
  3. additionThe chromatography fractions containing the product
  4. customthe solid recrystallized

Sources & evidence

ORD record
ord-6f33dd1c27134453b4f23de06535a6ec
Source dataset
uspto-grants-1987_03
Patent number
US04654343

Reaction notes

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