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

HRID 1906817
Notes
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Reaction equation

HRID 1906817 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6344
Dichloromethane
Solvent

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 recrystallized 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 recrystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-d4a595eece4246ceba3105b8bb4fc94f
Source dataset
uspto-grants-1987_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04654343

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes