Aniline → HCID 86611754, compound

HRID 2239878Notes

Reaction equation

HRID 2239878 reaction equation
Br[C:2]1[C:3]2[N:4]([CH:11]=[CH:12][N:13]=2)[N:5]=[C:6]([Cl:10])[C:7]=1[CH2:8][CH3:9].[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CC(C)([O-])C.[K+]>CN(C=O)C>[Cl:10][C:6]1[C:7]([CH2:8][CH3:9])=[C:2]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:3]2[N:4]([CH:11]=[CH:12][N:13]=2)[N:5]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 23665647Potassium tert-butoxideHCID 86611753HCID 86611753, compound

Product 1

HCID 86611754HCID 86611754, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 8-bromo-6-chloro-7-ethylimidazo[1,2-b]pyridazine (60 mg, 0.2 mmol, 1 eq) from 1d, aniline (20.3 μL, 0.22 mmol, 1.1 eq) and potassium tert-butoxide (0.51 mL, 0.51 mmol, 2.5 eq) were suspended in DMF (3 mL) and stirred at RT for 1 h. The mixture was quenched with ethyl acetate and washed with lithium chloride saturated solution, dried with sodium sulfate and concentrated in vacuo. The residue was purified using an ISCO chromatography system (4 g silica cartridge, 5% ethyl acetate in heptane) to provide 6-chloro-N-phenyl-7-ethylimidazo[1,2-b]pyridazin-8-amine (22 mg). LC/MS, m/e 273.14 (M+1). HPLC Rt, 2.24 min. Waters Sunfire C18 column (4.6×50 mm). 0%-100% B. Solvent B: (90% MeOH, 10% H2O, 0.1% TFA). Solvent A: (10% MeOH, 90% H2O, 0.1% TFA). Gradient, start % B=0, final % B=100, gradient time 4 min, hold at 100% B 1 min, flow rate 4 mL/min.

Workup

  1. customThe mixture was quenched with ethyl acetate
  2. washwashed with lithium chloride saturated solution
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified

Sources & evidence

ORD record
ord-508a4496976e4d259e44ed69569826e4
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Reaction notes

Loading…