Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | HCID 67372740 | HCID 67372740 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 58438355 | HCID 58438355 | — |
Reaction Steps
A solution of 5-(4-benzyloxy-phenyl)-6-butyl-pyridazine-3-carboxylic acid piperidin-4-ylamide dihydrochloride salt (0.096 mmol, 50 mg) and paraformaldehyde (0.96 mmol, 87 mg) in DCM was stirred for 20 min, and then sodium triacetoxyborohydride (0.96 mmol, 204 mg) was added, and stirring continued over night. The solvent was evaporated and to the residue was added saturated NaHCO3 solution, and extracted with ethyl acetate. The organic layer was washed with water, brine, dried (Na2SO4), filtered, and concentrated under reduced pressure. The resultant product was purified by column chromatography using 5% methanolic solution of ammonia (2.0 M ammonia in methanol) in DCM to provide 5-(4-benzyloxy-phenyl)-6-butyl-pyridazine-3-carboxylic acid (1-methyl-piperidin-4-yl)-amide LCMS: m/z 460.3 [M+2].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08431575B2 |
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| Source dataset | uspto-grants-2013_04 |
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| ORD ID | ord-111c0ce34a8c4d41830d236664fb378b |
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| Source note | uspto-grants-2013_04 |
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