HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl Acetate → Methyl 4-((3-chloropyrazin-2-yl)(2-cyanoacetamido)methyl)benzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Cyanoacetic acid | HCID 9740 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | Methyl 4-(amino(3-chloropyrazin-2-yl)methyl)benzoate | HCID 90303493 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Methyl 4-((3-chloropyrazin-2-yl)(2-cyanoacetamido)methyl)benzoate | HCID 90303780 | 100% |
Reaction Steps
To a solution of methyl 4-(amino(3-chloropyrazin-2-yl)methyl)benzoate (54 g, 195 mmol) in THF (500 mL) was added 2-cyanoacetic acid (16.6 g, 195 mmol) and TEA (39.4 g, 390 mmol). The mixture was added HATU (74.1 g, 195 mmol) at 0-5° C., and stirred at room temperature for 1 h. The reaction mixture was extracted with EA and water, the organic layer was dried and concentrated. The residue was purified by column chromatography on silica gel eluted with PE:EA=2:1 to give methyl 4-((3-chloropyrazin-2-yl)(2-cyanoacetamido)methyl)benzoate (67 g, yield 100%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09446130B2 |
| Source dataset | uspto-grants-2016_09 |
| ORD ID | ord-59b5ecf5a81a4010a58741e1d02b2447 |
| Source note | uspto-grants-2016_09 |