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

HRID 1528052Notes

Reaction equation

HRID 1528052 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.Cl.[Cl:31][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>[Cl:31][C:32]1[CH:33]=[C:34]([N:38]2[C:5]([C:7]3[C:12](=[O:13])[C:11]([O:14][CH3:15])=[CH:10][N:9]([C:16]4[CH:21]=[CH:20][C:19]([N:22]5[CH:26]=[CH:25][CH:24]=[N:23]5)=[CH:18][C:17]=4[O:27][CH3:28])[N:8]=3)=[CH:4][CH:3]=[N:39]2)[CH:35]=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 75331m-Chlorophenylhydrazine hydrochlorideHCID 71272086HCID 71272086, compound

Product 1

HCID 680146983-[1-(3-chlorophenyl)-1H-pyrazol-5-yl]-5-methoxy-1-[2-methoxy-4-(1H-pyrazol-1-yl)phenyl]pyridazin-4(1H)-oneYield 41.6%

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-chlorophenylhydrazine hydrochloride (67.7 mg) and TFA (0.15 mL) in ethanol (1.5 mL), and the mixture was stirred at room temperature for 5 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, ethyl acetate), crystallized from ethyl acetate, and recrystallized from ethanol/water to give the title compound (68.0 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. customcrystallized from ethyl acetate
  4. customrecrystallized from ethanol/water

Sources & evidence

ORD record
ord-aa2d35da49034bd6b4ab254b8820d114
Source dataset
uspto-grants-2015_07
Patent number
US09090586B2

Reaction notes

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