Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Dimethylamine | HCID 674 | — |
| 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 69936600 | HCID 69936600 | — |
Reaction Steps
Dimethylamine (60 uL, 0.33 mmol) and acetic acid (19 uL, 0.33 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, 0.33 mmol) in DCE (5 ml). The solution was stirred for 3 hours at 50° C. then sodium triacetoxyborohydride (105 mg, 0.50 mmol) was added. The mixture was stirred overnight. Saturated NaHCO3 solution (5 ml) was then added and the mixture was stirred for 5 minutes. The organic layer was diluted with dichloromethane (5 ml), separated and dried (MgSO4). The solvent was removed in vacuo and the residue purified by MDAP to yield the title compound as an opaque solid. 17 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-d1d2f26ccf304bd9950d99fe020b647a |
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| Source note | uspto-grants-2014_07 |
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