Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Morpholine | HCID 8083 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | HCID 86668211 | HCID 86668211 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 69936850 | HCID 69936850 | — |
Reaction Steps
Morpholine (0.05 ml, 0.54 mmol) and acetic acid (0.03 ml, 0.54 mmol) were added to a solution of 2-{[(3,4-difluorophenyl)methyl]oxy}-5-formyl-N-4-pyridazinylbenzamide (may be prepared by Example 79; 200 mg, 0.54 mmol) in DCE (5 ml), and the mixture was stirred at room temperature for 10 min. Sodium triacetoxyborohydride (172 mg, 0.81 mmol) was then added and the mixture was stirred at 50° C. overnight. Saturated sodium hydrogencarbonate (10 ml) was added and the mixture stirred for 10 min before being diluted with dichloromethane (25 ml). The organic layer was separated and the aqueous phase was extracted with dichloromethane (25 ml). The organics were combined and evaporated under reduced pressure. The residue was purified by MDAP to yield the title compound. 147 mg.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08778939B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-591c0ffb5c4d43a48c2c9d5d675fd547 |
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| Source note | uspto-grants-2014_07 |
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