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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 255198Generated: October 29, 2026

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

https://huagongshe.com/reaction/255198

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium triacetoxyborohydrideHCID 5049666—
Reactant3-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehydeHCID 21873737—
ReactantCis(+/-)1-{2-[4-amino-3-hydroxypiperidin-1-yl]ethyl}-5,7-difluoroquinolin-2(1H)-oneHCID 86642607—
ProductCis(+/-)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)-oneHCID 8664260671%

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07875715B2
Source datasetuspto-grants-2011_01
ORD IDord-5a512c6f33eb498ca6151e476c475809
Source noteuspto-grants-2011_01