Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 6-Amino-4-chloro-3-pyridinecarbonitrile | HCID 21949219 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 118036974 | HCID 118036974 | — |
Reaction Steps
6-Amino-4-chloronicotinonitrile (intermediate 16, 40 mg, 0.260 mmol) and EtOH (0.076 ml, 1.302 mmol) were charged into a sealed vial. NMP (1.5 ml) was added to the mixture at room temperature followed by NaH (60% dispersion in mineral oil, 62.5 mg, 1.56 mmol). The mixture was then heated at 70° C. for 2.5 days. The reaction mixture was diluted in EtOAc and washed with water (2×) and brine. The org. layer was dried over Na2SO4, filtered and concentrated under vacuum. The crude material was purified by normal phase chromatography (4 g silica gel cartridge, heptanes/EtOAc 100:0 to 0:100) to give the title compound as a beige solid. (UPLC-MS 1) tR 0.50 min; ESI-MS 164.0 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09266883B2 |
|---|
| Source dataset | uspto-grants-2016_02 |
|---|
| ORD ID | ord-6a66fcc49ccf4378adb056363f63020a |
|---|
| Source note | uspto-grants-2016_02 |
|---|