HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium hydride → Methyl 4-(2-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}ethyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Methyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate | HCID 2974054 | — |
| 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 | Methyl 4-(2-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}ethyl)-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate | HCID 66774852 | 85% |
Reaction Steps
Methyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate (Intermediate 86) (330 mg, 1.59 mmol) was deprotonated with sodium hydride and alkylated with 2-{4-[(tert-butoxycarbonyl)amino]piperidin-1-yl}ethyl methanesulfonate (Intermediate 6) (5.6 mmol) as described for Intermediate 2. Chromatography on silica gel with dichloromethane/methanol (20:1) gave the product in 85% yield as a yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07875715B2 |
| Source dataset | uspto-grants-2011_01 |
| ORD ID | ord-f8d42ec8d1464e19b2abb2d44309fdea |
| Source note | uspto-grants-2011_01 |