HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → 4-((4-((3R)-3-cyano-3-ethyl-2-oxopyrrolidin-1-yl)pyrimidin-2-yl)amino)-N-methylbenzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | 4-Amino-N-methylbenzamide | HCID 235516 | — |
| Reactant | (3R)-1-(2-chloropyrimidin-4-yl)-3-ethyl-2-oxopyrrolidine-3-carbonitrile | HCID 117840665 | — |
| Solvent | Isopropanol | HCID 3776 | — |
| Product | 4-((4-((3R)-3-cyano-3-ethyl-2-oxopyrrolidin-1-yl)pyrimidin-2-yl)amino)-N-methylbenzamide | HCID 117841029 | 41.8% |
Reaction Steps
A solution of (3R)-1-(2-chloropyrimidin-4-yl)-3-ethyl-2-oxopyrrolidine-3-carbonitrile (51 mg), 4-amino-N-methylbenzamide (32 mg) and acetic acid (12 μL) in 2-propanol (1 mL) was stirred in a microwave reactor at 150° C. for 1 hr. The reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate), and recrystallized (hexane/ethyl acetate) to give the title compound (31 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09187453B2 |
| Source dataset | uspto-grants-2015_11 |
| ORD ID | ord-97581dff194d41c191c6cd2bab29040d |
| Source note | uspto-grants-2015_11 |