Chloroacetone → 6-Chloro-2-methylimidazo(1,2-b)pyridazine

HRID 2205199Notes

Reaction equation

HRID 2205199 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH2:8])=[CH:4][CH:3]=1.Cl[CH2:10][C:11](=O)[CH3:12].C(N(CC)CC)C>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:10]=[C:11]([CH3:12])[N:8]=2)[N:7]=1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 8471TriethylamineHCID 216436-Amino-3-chloropyridazine

Product 1

HCID 104420726-Chloro-2-methylimidazo(1,2-b)pyridazineYield 80.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 6-chloropyridazin-3-amine (2.35 g, 18.1 mmol, 1.0 equiv) in ethanol (15 mL) was added 1-chloropropan-2-one (2.92 mL, 36.3 mmol, 2.0 equiv) and triethylamine (2.53 mL, 18.1 mmol, 1.0 equiv). The solution was heated at 150° C. for 30 min then quenched with water. Purification by column chromatography using 30% ethyl acetate in hexanes elution gave 2.43 g of the brown solid, 80%.

Workup

  1. customthen quenched with water
  2. customPurification by column chromatography
  3. wash30% ethyl acetate in hexanes elution

Sources & evidence

ORD record
ord-0d9a4f03b8304040ba63a17d87d5f7ab
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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