Trifluoroacetic acid → 3-[(2'-Carboxybiphen-4-yl)methyl]-6,8-dimethyl-2-ethylimidazo[1,2-b]pyridazine

HRID 257265Notes

Reaction equation

HRID 257265 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]2[C:10]([CH3:11])=[CH:9][C:8]([CH3:12])=[N:7][N:6]2[C:13]=1[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:33]=[CH:32][CH:31]=[CH:30][C:22]=2[C:23]([O:25]C(C)(C)C)=[O:24])=[CH:17][CH:16]=1)[CH3:2].C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>C(Cl)Cl>[C:23]([C:22]1[CH:30]=[CH:31][CH:32]=[CH:33][C:21]=1[C:18]1[CH:17]=[CH:16][C:15]([CH2:14][C:13]2[N:6]3[N:7]=[C:8]([CH3:12])[CH:9]=[C:10]([CH3:11])[C:5]3=[N:4][C:3]=2[CH2:1][CH3:2])=[CH:20][CH:19]=1)([OH:25])=[O:24]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 19784151t-Butyl 2-[4-[(2-ethyl-6,8-dimethylimidazo[1,2-b]pyridazin-3-yl)methyl]phenyl]benzoate

Product 1

HCID 443105903-[(2'-Carboxybiphen-4-yl)methyl]-6,8-dimethyl-2-ethylimidazo[1,2-b]pyridazineYield 86.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.111 g (0.25 mmol) of the product of Step H and 0.055 g (0.51 mmol) of anisole dissolved in 0.25 mL of methylene chloride was added 0.4 mL of trifluoroacetic acid and the reaction mixture was stirred under a nitrogen atmosphere at room temperature for 14 hours. The reaction mixture was then evaporated in vacuo and purified on a silica gel flash chromatography column eluted with CHCl3 -MeOH-NH4OH (80:15:1). Evaporation of the purified fractions and drying in vacuo afforded 0.083 g (86%) of the title compound as a white amorphous solid.

Workup

  1. customThe reaction mixture was then evaporated in vacuo
  2. custompurified on a silica gel flash chromatography column
  3. washeluted with CHCl3 -MeOH-NH4OH (80:15:1)
  4. customEvaporation of the purified fractions
  5. customdrying in vacuo

Sources & evidence

ORD record
ord-54da801fe5c94284bf38b14b103e973f
Source dataset
uspto-grants-1993_11
Patent number
US05260285

Reaction notes

Loading…