HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium hydride → tert-Butyl {3-[2-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]-3-azabicyclo[3.1.0]hex-6-yl}carbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 3-Oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbonitrile | HCID 10654813 | — |
| Reactant | tert-butyl {1-[2-(7-methoxy-2-oxoquinolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate | HCID 59371209 | — |
| Reactant | 2-{6-[(Tert-butoxycarbonyl)amino]-3-azabicyclo[3.1.0]hex-3-yl)ethyl methanesulfonate | HCID 86642626 | — |
| Solvent | Dichloromethane methanol | HCID 21226129 | — |
| Product | tert-Butyl {3-[2-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]-3-azabicyclo[3.1.0]hex-6-yl}carbamate | HCID 86642625 | 94% |
Reaction Steps
3-Oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbonitrile (Intermediate 60) (231 mg, 1.5 mmol) was deprotonated with sodium hydride and alkylated with 2-{6-[(tert-butoxycarbonyl)amino]-3-azabicyclo[3.1.0]hex-3-yl}ethyl methanesulfonate (Intermediate 95) (1.55 mmol) as described for Intermediate 2. Chromatography on silica gel with dichloromethane/methanol (20:1) gave 442 mg (94%) product as a yellow gum.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07875715B2 |
| Source dataset | uspto-grants-2011_01 |
| ORD ID | ord-9b51bbe5e2834fff8f2f1ccc03c8561d |
| Source note | uspto-grants-2011_01 |