Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Propanal | HCID 527 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | HCID 22024327 | HCID 22024327 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 22024440 | HCID 22024440 | — |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07772249B2 |
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| Source dataset | uspto-grants-2010_08 |
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| ORD ID | ord-8214c6756f37497d9993db23a03d31fe |
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| Source note | uspto-grants-2010_08 |
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