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

HRID 226006Notes

Reaction equation

HRID 226006 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.C(OCC)(=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

6

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 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Heat 850 mg (4.74 mmol) of 4-(1-ethyl-propyl)-6-methyl-pyridazin-3-ylamine and 0.415 ml (5.22 ml) of chloroacetone in 20 ml of ethanol in microwave at 110° C. for 35 minutes. Add 1.2 g (14.2 mmol) of sodium bicarbonate and heat in oil bath with reflux condensor at 100° C. overnight. Evaporate solvents, take up in ethyl acetate and wash 3 X's with brine. Dry over sodium sulfate, filter, and evaporate to a brown oil. Chromatograph using hexanes to 6:1 hex:ethyl acetate to ethyl acetate gradient. Collect title compound as oil weighing 3.69 g (17.0 mmol, 84.4%). 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. temperatureheat in oil bath
  2. washwash 3 X's with brine
  3. dry with materialDry over sodium sulfate
  4. filtrationfilter
  5. customevaporate to a brown oil
  6. customCollect title compound as oil

Sources & evidence

ORD record
ord-ad64525561bf415086741cde13f8d4b5
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Reaction notes

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