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

HRID 1906813Notes

Reaction equation

HRID 1906813 reaction equation
C(O[C:4](=[O:6])C)=O.ClCCl.[CH3:10][C:11]1[N:15]2[N:16]=[C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([NH2:26])[CH:21]=3)[CH:18]=[CH:19][C:14]2=[N:13][N:12]=1>ClCCl.CO>[CH3:10][C:11]1[N:15]2[N:16]=[C:17]([C:20]3[CH:21]=[C:22]([NH:26][CH:4]=[O:6])[CH:23]=[CH:24][CH:25]=3)[CH:18]=[CH:19][C:14]2=[N:13][N:12]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 75269Acetic-formic anhydrideHCID 127268683-Methyl-6-[3-(amino)phenyl]-1,2,4-triazolo[4,3-b]pyridazine

Product 1

HCID 15595683N-[3-(3-Methyl-1,2,4-triazolo-[4,3-b]pyridazin-6-yl) phenyl]formamide

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To 5.53 ml of acetic-formic anhydride was added 250 ml dichloromethane followed by 10 g of 3-methyl-6-[3-(amino)-phenyl]-1,2,4-triazolo[4,3-b]pyridazine. The solution was stirred for 12 hours, then diluted with 1 liter of dichloromethane-methanol (9:1). This solution was washed with saturated aqueous sodium bicarbonate, dried, and concentrated in vacuo. The residue was recrystallized from dichloromethane-methanol to give 6.7 g of an off-white powder, mp 265°-268° C.

Workup

  1. washThis solution was washed with saturated aqueous sodium bicarbonate
  2. customdried
  3. concentrationconcentrated in vacuo
  4. customThe residue was recrystallized from dichloromethane-methanol

Sources & evidence

ORD record
ord-ae646a2cbf48428593929ffc6eb4fc9d
Source dataset
uspto-grants-1987_03
Patent number
US04654343

Reaction notes

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