Chloroacetone → 2,6-Dimethyl-8-(1-propyl-butyl)-imidazo[1,2-b]pyridazine

HRID 1432676Notes

Reaction equation

HRID 1432676 reaction equation
[CH3:1][C:2]1[N:7]=[N:6][C:5]([NH2:8])=[C:4]([CH:9]([CH2:13][CH2:14][CH3:15])[CH2:10][CH2:11][CH3:12])[CH:3]=1.Cl[CH2:17][C:18](=O)[CH3:19].C([O-])(O)=O.[Na+]>C(O)C>[CH3:19][C:18]1[N:8]=[C:5]2[C:4]([CH:9]([CH2:13][CH2:14][CH3:15])[CH2:10][CH2:11][CH3:12])=[CH:3][C:2]([CH3:1])=[N:7][N:6]2[CH:17]=1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 516892Sodium BicarbonateHCID 688399026-Methyl-4-(1-propyl-butyl)-pyridazin-3-ylamine

Product 1

HCID 688409972,6-Dimethyl-8-(1-propyl-butyl)-imidazo[1,2-b]pyridazineYield 70.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

A 250 mL round bottom flask is charged with 6-methyl-4-(1-propyl-butyl)-pyridazin-3-ylamine (0.611 g, 0.00295 moles, 1 equiv), ethanol 2B (30 mL), and chloroacetone (0.382 g, 0.328 ml, 0.00412 moles, 1.4 equiv). The reaction mixture is heated at 75° C. overnight and then cooled to room temp. NaHCO3 (0.371 g, 0.00442 moles, 1.5 equiv) is slowly added to the reaction mixture that is then heated to 100° C. overnight. The reaction mixture is cooled and the solvent is evaporated. Dichloromethane is added and the reaction mixture is passed through filter paper. The solvent is evaporated to obtain a brown oil which is purified via silica gel chromatography. The material is eluted with a hexanes and ethyl acetate gradient to obtain 0.511 g of the final products. Two peaks are identified in the lc/ms. The mixture is used “as is” in the next reaction. MS (APCI): 246 (M+1).

Workup

  1. temperaturecooled to room temp
  2. temperatureis then heated to 100° C. overnight
  3. temperatureThe reaction mixture is cooled
  4. customthe solvent is evaporated
  5. additionDichloromethane is added
  6. filtrationthrough filter paper
  7. customThe solvent is evaporated
  8. customto obtain a brown oil which
  9. customis purified via silica gel chromatography
  10. washThe material is eluted with a hexanes and ethyl acetate gradient

Sources & evidence

ORD record
ord-0726c82e4f3544fbbd9be0dd279a282c
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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