Water → N-[3-(3-Methyl-1,2,4-triazolo[4,3-b]pyridazin-6-yl)phenyl]butanamide

HRID 329640Notes

Reaction equation

HRID 329640 reaction equation
[CH3:1][C:2]1[N:6]2[N:7]=[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([NH2:17])[CH:12]=3)[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1.C(N(C(C)C)CC)(C)C.[C:27](Cl)(=[O:31])[CH2:28][CH2:29][CH3:30].O>ClCCl>[CH3:1][C:2]1[N:6]2[N:7]=[C:8]([C:11]3[CH:12]=[C:13]([NH:17][C:27](=[O:31])[CH2:28][CH2:29][CH3:30])[CH:14]=[CH:15][CH:16]=3)[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8855Butyryl chlorideHCID 81531DiisopropylethylamineHCID 127268683-Methyl-6-[3-(amino)phenyl]-1,2,4-triazolo[4,3-b]pyridazine

Product 1

HCID 7532414N-[3-(3-Methyl-1,2,4-triazolo[4,3-b]pyridazin-6-yl)phenyl]butanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6 g of 3-methyl-6-[3-(amino)-phenyl]-1,2,4-triazolo [4,3-b]pyridazine and 5.1 ml diisopropylethylamine in 500 ml dichloromethane was added 3.1 ml of butyryl chloride. This solution was stirred for 12 hours then poured onto 200 ml of water and extracted with 150 ml portions of dichloromethane. The combined extracts were dried, concentrated in vacuo and the solid chromatographed on 500 g silica gel with dichloromethane-methanol (95:5). The fractions containing the desired product were combined, concentrated in vacuo and the solid recrystalized from dichloromethane-hexane to give.5.58 g of white crystals, mp 195°-198° C.

Workup

  1. extractionextracted with 150 ml portions of dichloromethane
  2. customThe combined extracts were dried
  3. concentrationconcentrated in vacuo
  4. customthe solid chromatographed on 500 g silica gel with dichloromethane-methanol (95:5)
  5. additionThe fractions containing the desired product
  6. concentrationconcentrated in vacuo
  7. customthe solid recrystalized from dichloromethane-hexane
  8. customto give

Sources & evidence

ORD record
ord-b5f6f74a7e9249b191334411dbb11949
Source dataset
uspto-grants-1990_01
Patent number
US04892873

Reaction notes

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