Chloroacetone → 2,6-Dimethyl-8-(pentan-3-yl)imidazo[1,2-b]pyridazine

HRID 1432563Notes

Reaction equation

HRID 1432563 reaction equation
[CH2:1]([CH:3]([C:6]1[CH:11]=[C:10]([CH3:12])[N:9]=[N:8][C:7]=1[NH2:13])[CH2:4][CH3:5])[CH3:2].Cl[CH2:15][C:16](=O)[CH3:17].C(=O)(O)[O-].[Na+]>C(O)C>[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([CH:15]=[C:16]([CH3:17])[N:13]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 516892Sodium BicarbonateHCID 534216106-Methyl-4-(pentan-3-YL)pyridazin-3-amine

Product 1

HCID 688412672,6-Dimethyl-8-(pentan-3-yl)imidazo[1,2-b]pyridazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

4-(1-Ethyl-propyl)-6-methyl-pyridazin-3-ylamine (850 mg, 4.74 mmol), chloroacetone (0.415 ml, 5.22 mL) and 20 mL of ethanol are heated in the microwave at 110° C. for 35 minutes. Sodium bicarbonate (1.2 g, 14.2 mmol) is added, and the reaction mixture is heated in an oil bath at 100° C. overnight. The solvent is evaporate and the residue is taken up in ethyl acetate and washed three times with brine. The organic layer is dried over sodium sulfate, filtered, and evaporated to a brown oil. The crude product is purified via silica gel chromatography using a hexane:ethyl acetate gradient. The title compound is an oil weighing 3.69 g (17.0 mmol, 84%). 1H-NMR (DMSO-d6), δ 7.34 (s, 1H); 6.84 (s, 1H); 2.85-3.10 (m, 1H); 2.43 (s, 3H); 2.32 (s, 3H); 1.70-1.80 (m, 4H); 0.712 (t, J=7.49 Hz, 6H) ppm. MS/ES+=219 (100%, M+2).

Workup

  1. customThe solvent is evaporate
  2. washwashed three times with brine
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated to a brown oil
  6. customThe crude product is purified via silica gel chromatography

Sources & evidence

ORD record
ord-120f55fd8c314f1cb6b9e4aa32b238e4
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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