Acetic Acid → HCID 59436243, compound

HRID 1624747Notes

Reaction equation

HRID 1624747 reaction equation
[O:1]=[C:2]1[CH:7]=[CH:6][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[N:4]=[C:3]1[C:18]([NH:20][NH2:21])=O.CO[CH:24](OC)[N:25]([CH3:27])C.C(O)(=O)C.N[C:35]1[CH:40]=[CH:39]C=[CH:37][CH:36]=1>C(#N)C>[C:24]1([N:25]2[CH:27]=[N:21][N:20]=[C:18]2[C:3]2[C:2](=[O:1])[CH:7]=[CH:6][N:5]([C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=3)[N:4]=2)[CH:39]=[CH:40][CH:35]=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6115AnilineHCID 78373Dimethylformamide dimethyl acetalHCID 59436165HCID 59436165, compound

Product 1

HCID 59436243HCID 59436243, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
125 °C

Procedure

A solution of 4-oxo-1-[3-(trifluoromethyl)phenyl]-1,4-dihydropyridazine-3-carbohydrazide (0.2 g, 0.67 mmol) and N,N-dimethylformamide dimethylacetal (0.09 mL, 0.67 mmol) in acetonitrile (2 mL) was heated at 55° C. for 45 min. After that time, acetic acid (2 mL) and aniline (0.06 mL, 0.66 mmol) were added and the temperature was increased to 125° C. for an additional 2 h. During this time, the acetonitrile was allowed to distill-off. The reaction was then concentrated to a dark residue and the crude product purified by column chromatography (silica gel, ethyl acetate to 4:1 ethyl acetate/methanol) to give 3-(4-phenyl-4H-1,2,4-triazol-3-yl)-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one (0.137 g, 53%) as a light yellow oil that crystallized upon standing.

Workup

  1. concentrationThe reaction was then concentrated to a dark residue
  2. customthe crude product purified by column chromatography (silica gel, ethyl acetate to 4:1 ethyl acetate/methanol)

Sources & evidence

ORD record
ord-df07c026cb2e4a6fbd757a6f928c36ee
Source dataset
uspto-grants-2014_07
Patent number
US08778944B2

Reaction notes

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