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

HRID 1528047Notes

Reaction equation

HRID 1528047 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[F:27])[N:8]=1)=O.[F:29][C:30]([F:35])([F:34])[CH2:31][NH:32][NH2:33].C(O)(C(F)(F)F)=O>C(O)C>[F:27][C:17]1[CH:18]=[C:19]([N:22]2[CH:26]=[CH:25][CH:24]=[N:23]2)[CH:20]=[CH:21][C:16]=1[N:9]1[CH:10]=[C:11]([O:14][CH3:15])[C:12](=[O:13])[C:7]([C:5]2[N:32]([CH2:31][C:30]([F:35])([F:34])[F:29])[N:33]=[CH:3][CH:4]=2)=[N:8]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 787402,2,2-TrifluoroethylhydrazineHCID 712721203-[3-(dimethylamino)prop-2-enoyl]-1-[2-fluoro-4-(1H-pyrazol-1-yl)phenyl]-5-methoxypyridazin-4(1H)-one

Product 1

HCID 680146991-[2-fluoro-4-(1H-pyrazol-1-yl)phenyl]-5-methoxy-3-[1-(2,2,2-trifluoroethyl)-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-fluoro-4-(1H-pyrazol-1-yl)phenyl]pyridazin-4(1H)-one (200 mg) in ethanol (2.0 mL) was added dropwise a solution of 2,2,2-trifluoroethylhydrazine (0.0483 mL) and TFA (0.2 mL) in ethanol (2.0 mL), and the mixture was stirred at room temperature for 48 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (170 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-328bf34156b14349806097335ac37e5c
Source dataset
uspto-grants-2015_07
Patent number
US09090586B2

Reaction notes

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