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 86668210 | HCID 86668210 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 69936766 | HCID 69936766 | — |
Reaction Steps
Morpholine (26 uL, 0.30 mmol) and acetic acid (17 ul, 0.30 mmol) were added to a solution of 5-formyl-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide (may be prepared as described in Example 66; 100 mg, 0.301 mmol) in DCE (5 ml). The solution was stirred for 4 hours at 50° C. then sodium triacetoxyborohydride (96 mg, 0.45 mmol) was added. The reaction was stirred overnight. Saturated NaHCO3 solution (5 ml) was added and the mixture stirred for 5 minutes. The organic layer was then diluted with dichloromethane (5 ml) before being separated and dried (MgSO4). The solvent was removed in vacuo and the residue purified by MDAP to yield the title compound. 40 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-5824787b23fa41029d67c06b88bdcd0a |
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| Source note | uspto-grants-2014_07 |
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