Trifluoroacetic acid → 5-methoxy-1-[2-methoxy-4-(1H-pyrazol-1-yl)phenyl]-3-{1-[3-(trifluoromethyl)phenyl]-1H-pyrazol-5-yl}pyridazin-4(1H)-one

HRID 1528051Notes

Reaction equation

HRID 1528051 reaction equation
CN(C)[CH:3]=[CH:4][C:5]([C:7]1[C:12](=[O:13])[C:11]([O:14][CH3:15])=[CH:10][N:9]([C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH:26]=[CH:25][CH:24]=[N:23]3)=[CH:18][C:17]=2[O:27][CH3:28])[N:8]=1)=O.[F:30][C:31]([F:41])([F:40])[C:32]1[CH:33]=[C:34]([NH:38][NH2:39])[CH:35]=[CH:36][CH:37]=1.C(O)(C(F)(F)F)=O>C(O)C>[CH3:15][O:14][C:11]1[C:12](=[O:13])[C:7]([C:5]2[N:38]([C:34]3[CH:35]=[CH:36][CH:37]=[C:32]([C:31]([F:40])([F:41])[F:30])[CH:33]=3)[N:39]=[CH:3][CH:4]=2)=[N:8][N:9]([C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH:26]=[CH:25][CH:24]=[N:23]3)=[CH:18][C:17]=2[O:27][CH3:28])[CH:10]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 98650(3-(Trifluoromethyl)phenyl)hydrazineHCID 71272086HCID 71272086, compound

Product 1

HCID 712720315-methoxy-1-[2-methoxy-4-(1H-pyrazol-1-yl)phenyl]-3-{1-[3-(trifluoromethyl)phenyl]-1H-pyrazol-5-yl}pyridazin-4(1H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a suspension of 3-[3-(dimethylamino)prop-2-enoyl]-5-methoxy-1-[2-methoxy-4-(1H-pyrazol-1-yl)phenyl]pyridazin-4(1H)-one (136 mg) in ethanol (1.5 mL) was added dropwise a solution of 3-(trifluoromethyl)phenylhydrazine (0.049 mL) and TFA (0.15 mL) in ethanol (1.5 mL), and the mixture was stirred at room temperature for 3 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, ethyl acetate), and recrystallized from ethanol/water to give the title compound (123 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (NH, ethyl acetate)
  3. customrecrystallized from ethanol/water

Sources & evidence

ORD record
ord-eec7095a64404c76a88f1efca44807db
Source dataset
uspto-grants-2015_07
Patent number
US09090586B2

Reaction notes

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