HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium triacetoxyborohydride → Cis(+/-)6-[({1-[2-(5,7-difluoro-2-oxoquinolin-1(2H)-yl)ethyl]-3-hydroxypiperidin-4-yl}amino)methyl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | 3-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehyde | HCID 21873737 | — |
| Reactant | Cis(+/-)1-{2-[4-amino-3-hydroxypiperidin-1-yl]ethyl}-5,7-difluoroquinolin-2(1H)-one | HCID 86642607 | — |
| Product | Cis(+/-)6-[({1-[2-(5,7-difluoro-2-oxoquinolin-1(2H)-yl)ethyl]-3-hydroxypiperidin-4-yl}amino)methyl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one | HCID 86642606 | 71% |
Reaction Steps
Cis(±)1-{2-[4-amino-3-hydroxypiperidin-1-yl]ethyl}-5,7-difluoroquinolin-2(1H)-one (175 mg, 0.54 mmol), 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehyde (WO 2004/058144) (96 mg, 0.54 mmol) and sodium triacetoxy borohydride (344 mg, 1.6 mmol) were reacted as described for Example 1 to give 186 mg (71%) of the free base of the product as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07875715B2 |
| Source dataset | uspto-grants-2011_01 |
| ORD ID | ord-5a512c6f33eb498ca6151e476c475809 |
| Source note | uspto-grants-2011_01 |