Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 4-Chloro-3-nitropyridine | HCID 2735781 | — |
| Reactant | HCID 178472433 | HCID 178472433 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 178501201 | HCID 178501201 | 76% |
Reaction Steps
A round bottom flask under nitrogen atmosphere was charged with 4-chloro-3-nitropyridine (1.65 g, 10.41 mmol), cis-ethyl 4-aminocyclohexanecarboxylate (2.454 g, 15.61 mmol), and ACN (26 mL). To the mixture was added DIPEA (3.63 mL, 20.81 mmol). The resulting mixture was stirred at 60° C. for 17 hours. The reaction was stopped, cooled to RT and diluted with water (20 mL) and DCM (50 mL). The layers were separated, and the organic layer was collected, dried over sodium sulfate and concentrated to afford an orange oil. The oil was purified by silica gel chromatography to afford the title compound (2.2 g, 76% yield) as a bright yellow solid. MS m/z=280.2 [M+H]. Calc'd for C13H17N3O4: 279.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09115127B2 |
|---|
| Source dataset | uspto-grants-2015_08 |
|---|
| ORD ID | ord-60184fe277274f098705ff142f38a7af |
|---|
| Source note | uspto-grants-2015_08 |
|---|