HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium hydride → tert-Butyl{1-[2-(7-bromo-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-1-yl)ethyl]piperidin-4-yl}carbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 6-Bromo-2H-pyrido[3,2-B][1,4]oxazin-3(4H)-one | HCID 21873772 | — |
| Reactant | 2-(4-((Tert-butoxycarbonyl)amino)piperidin-1-yl)ethyl methanesulfonate | HCID 56834478 | — |
| Reactant | tert-butyl {1-[2-(7-methoxy-2-oxoquinolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate | HCID 59371209 | — |
| Solvent | Dichloromethane methanol | HCID 21226129 | — |
| Product | tert-Butyl{1-[2-(7-bromo-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-1-yl)ethyl]piperidin-4-yl}carbamate | HCID 86642663 | 93% |
Reaction Steps
6-Bromo-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one (Intermediate 211) (460 mg, 2.0 mmol) was deprotonated with sodium hydride and alkylated with 2-{4-[tert-butoxycarbonyl)amino]piperidin-1-yl}ethyl methanesulfonate (Intermediate 6) (2.1 mmol) as described for Intermediate 2. Chromatography on silica gel with methanol/dichloromethane gave the product as an oil (0.85 g, 93% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08124602B2 |
| Source dataset | uspto-grants-2012_02 |
| ORD ID | ord-28431ad0302342babce37595bc079d4c |
| Source note | uspto-grants-2012_02 |