Acetic Acid → HCID 58072174, compound

HRID 1805649Notes

Reaction equation

HRID 1805649 reaction equation
[C:1]([C:4]1[C:9](=[O:10])[C:8]([Br:11])=[CH:7][N:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[N:5]=1)(=O)[CH3:2].[CH3:22]OC(OC)N(C)C.CC(O)=O.[C:34]1([NH:40][NH2:41])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>Cl>[Br:11][C:8]1[C:9](=[O:10])[C:4]([C:1]2[N:40]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[N:41]=[CH:22][CH:2]=2)=[N:5][N:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7516Phenylhydrazine2×HCID 78373Dimethylformamide dimethyl acetalHCID 58072286HCID 58072286, compound

Product 1

HCID 58072174HCID 58072174, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 3-acetyl-5-bromo-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one (332 mg, 0.92 mmol) and N,N-dimethylformamide dimethyl acetal (3.3 mL) was heated to reflux for 1 h. The mixture was concentrated in vacuo. To the residue were added AcOH (3.3 mL) and phenylhydrazine (0.181 mL, 1.84 mmol). The mixture was heated to reflux for 90 min. To the mixture was added phenylhydrazine (0.091 mL, 0.92 mmol). The mixture was heated to reflux for 90 min. The mixture was diluted with 1 M HCl aqueous solution, extracted with AcOEt, washed with saturated NaHCO3 aqueous solution, dried over MgSO4, filtered, concentrated in vacuo and purified by column chromatography on basic silica gel (hexane/AcOEt=50/50 to 0/100) and by HPLC to yield the title compound (151 mg, 35% yield) as a white solid: mp 145-146° C. 1H NMR (DMSO-d6, 300 MHz): δ ppm 7.27 (1H, d, J=1.9 Hz), 7.35-7.52 (6H, m), 7.54-7.64 (2H, m), 7.73 (1H, d, J=8.0 Hz), 7.85 (1H, d, J=1.9 Hz), 9.52 (1H, s). Anal. Calcd for C20H12BrF3N4O: C, 52.08; H, 2.62; N, 12.15. Found: C, 52.07; H, 2.75; N, 12.28.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 h
  3. concentrationThe mixture was concentrated in vacuo
  4. temperatureThe mixture was heated
  5. temperatureto reflux for 90 min
  6. temperatureThe mixture was heated
  7. temperatureto reflux for 90 min
  8. extractionextracted with AcOEt
  9. washwashed with saturated NaHCO3 aqueous solution
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. custompurified by column chromatography on basic silica gel (hexane/AcOEt=50/50 to 0/100) and by HPLC

Sources & evidence

ORD record
ord-84e0e4b4f1514dada1a9ba152cc2c425
Source dataset
uspto-grants-2013_01
Patent number
US08354411B2

Reaction notes

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