Pivaloyl chloride → N-(3-(3-methyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)phenyl)pivalamide

HRID 35636Notes

Reaction equation

HRID 35636 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.[CH3:18][C:19]([CH3:24])([CH3:23])[C:20](Cl)=[O:21].C(N(C(C)C)CC)(C)C.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:18][C:19]([CH3:24])([CH3:23])[C:20]([NH: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)=[O:21]

Participants

6

Reactant 4

HCID 62493Pivaloyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 127268683-Methyl-6-[3-(amino)phenyl]-1,2,4-triazolo[4,3-b]pyridazine

Product 1

HCID 15595676N-(3-(3-methyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)phenyl)pivalamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To solution of 8.0 g of 3-methyl-6-[3-(amino)phenyl]-1,2,4-triazolo[4,3-b]pyridazine in 1.5 liters of dichloromethane was added 4.6 ml of trimethylacetyl chloride and 6.8 ml of diisopropylethylamine. The mixture was stirred for 3 hours and then poured into 200 ml of aqueous saturated sodium bicarbonate. The organic layer was separated, dried, and the solvent was removed in vacuo. The residue was recrystallized from dichloromethane-hexane to give 9.2 g of white crystals, mp 256°-258° C.

Workup

  1. customThe organic layer was separated
  2. customdried
  3. customthe solvent was removed in vacuo
  4. customThe residue was recrystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-6658129321d54d958c48e7951e0b52f8
Source dataset
uspto-grants-1988_08
Patent number
US04767765

Reaction notes

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