Methylamine → 5-methoxy-N-methyl-3-[3-(trifluoromethyl)phenyl]-4-pyridazinamine

HRID 54652Notes

Reaction equation

HRID 54652 reaction equation
F[C:2]1[C:7]([O:8][CH3:9])=[CH:6][N:5]=[N:4][C:3]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=1.[CH3:20][NH2:21]>O.C1COCC1>[CH3:9][O:8][C:7]1[C:2]([NH:21][CH3:20])=[C:3]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[N:4]=[N:5][CH:6]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 19959683HCID 19959683, compound

Product 1

HCID 199596815-methoxy-N-methyl-3-[3-(trifluoromethyl)phenyl]-4-pyridazinamineYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

4-Fluoro-5-methoxy-3-[3-(trifluoromethyl)phenyl]pyridazine (0.6 g, 0.0022 mole, Compound No. 46) and methylamine (1.54 g of a 40% solution in water, 0.0194 mole) were stirred at RT in THF (20 mL) under N2 for 24 h. The mixture was poured into water and extracted 3×50 mL with ethyl acetate. The organic layer was dried (MgSO4), filtered, and evaporated in vacuo. The crude solid was recrystallized from cyclohexane/ethyl acetate to give 5-methoxy-N-methyl-3-[3-(trifluoromethyl)phenyl]-4-pyridazinamine (0.59 g, 95% yield, Compound No. 86) as an off white solid.

Workup

  1. extractionextracted 3×50 mL with ethyl acetate
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe crude solid was recrystallized from cyclohexane/ethyl acetate

Sources & evidence

ORD record
ord-3ae1574957614b01a6c64a71b1990661
Source dataset
uspto-grants-1997_04
Patent number
US05623072

Reaction notes

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