Acetic Acid → HCID 22024440, compound

HRID 501027Notes

Reaction equation

HRID 501027 reaction equation
[CH:1](=O)[CH2:2][CH3:3].[CH3:5][C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:7]=1[C:13]1[C:14]2[N:15]([C:20]([NH2:25])=[C:21]([CH2:23][CH3:24])[N:22]=2)[N:16]=[C:17]([CH3:19])[CH:18]=1.C(O[BH-](O[C:36](=O)[CH3:37])OC(=O)C)(=O)C.[Na+].[C:40](O)(=O)C>ClCCl.O>[CH3:5][C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:7]=1[C:13]1[C:14]2[N:15]([C:20]([N:25]([CH2:40][CH2:36][CH3:37])[CH2:1][CH2:2][CH3:3])=[C:21]([CH2:23][CH3:24])[N:22]=2)[N:16]=[C:17]([CH3:19])[CH:18]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 527PropanalHCID 5049666Sodium triacetoxyborohydrideHCID 22024327HCID 22024327, compound

Product 1

HCID 22024440HCID 22024440, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Propionaldehyde (3.26 mL, 45.25 mmol) was added to a solution of the resulting 8-(2,4-dimethylphenyl)-2-ethyl-6-methylimidazo[1,2-b]pyridazin-3-amine (9.05 mmol) in dichloromethane (60 mL), and the mixture was stirred at room temperature for 10 minutes. Sodium triacetoxyborohydride (5.75 g, 27.15 mmol) was gradually added thereto, then acetic acid (1 mL) was further added dropwise, and the mixture was stirred for 5 hours. Water was added thereto, which was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate and evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:9) to give the title compound (8.8 mg) as a pale green oil.

Workup

  1. stirringthe mixture was stirred for 5 hours
  2. extractionwhich was extracted with ethyl acetate
  3. washThe organic layer was washed with an aqueous saturated sodium bicarbonate solution and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:9)

Sources & evidence

ORD record
ord-8214c6756f37497d9993db23a03d31fe
Source dataset
uspto-grants-2010_08
Patent number
US07772249B2

Reaction notes

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