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

HRID 35633Notes

Reaction equation

HRID 35633 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[CH2:23][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+].[CH2:26](I)[CH3:27].O>CN(C)C=O>[CH2:26]([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[CH2:23][CH2:22][CH2:21]1)=[O:19])[CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 15595670N-(3-(3-methyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)phenyl)cyclobutanecarboxamide

Product 1

HCID 15595671N-Ethyl-N-[3-(3-methyl-1,2,4-triazolo[4,3-b]pyridazin-6-yl)phenyl]cyclobutanecarboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.0 g of N-[3-(3-methyl-1,2,4-triazolo[4,3-b]pyridazin-6-yl)phenyl]cyclobutanecarboxamide and 0.36 g of sodium hydride (50% in oil) in 200 ml of dry dimethylformamide, under argon, was stirred for 1 hour, then 0.6 ml of ethyl iodide was added. This mixture was stirred overnight, then poured into 200 ml of water and extracted with dichloromethane. The extracts were combined, dried and evaporated in vacuo. The residue was chromatographed on a silica gel column, eluting with dichloromethane:methanol (97:3). The fractions containing product were combined and evaporated, giving 0.81 g of the desired compound as yellow crystals, mp 157°-159° C.

Workup

  1. stirringThis mixture was stirred overnight
  2. extractionextracted with dichloromethane
  3. customdried
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on a silica gel column
  6. washeluting with dichloromethane:methanol (97:3)
  7. additionThe fractions containing product
  8. customevaporated

Sources & evidence

ORD record
ord-ace0d014aba04e76872aeee5315dc352
Source dataset
uspto-grants-1988_08
Patent number
US04767765

Reaction notes

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