HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyrrolidine → Methyl 2'-cyano-4'-methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyrrolidine | HCID 31268 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 1-Hydroxybenzotriazole hydrate | HCID 2796029 | — |
| Reactant | 2'-Cyano-5-(methoxycarbonyl)-4'-methylbiphenyl-3-carboxylic acid | HCID 58188377 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Methyl 2'-cyano-4'-methyl-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxylate | HCID 58188323 | — |
Reaction Steps
To a mixture of 2′-cyano-5-(methoxycarbonyl)-4′-methylbiphenyl-3-carboxylic acid (0.20 g, 0.68 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.26 g, 1.4 mmol), 1-hydroxybenzotriazole hydrate (0.21 g, 1.4 mmol), and methylene chloride (10 mL) were added pyrrolidine (0.072 g, 1.0 mmol) and N,N-diisopropylethylamine (0.24 mL, 1.4 mmol). The mixture was stirred at room temperature overnight, and then concentrated. The residue was purified via flash chromatography (silica gel column, 0-100% EtOAc/hexane) to afford the desired product as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08946439B2 |
| Source dataset | uspto-grants-2015_02 |
| ORD ID | ord-f0983c482d7a4fd0bdc57da23d4164ae |
| Source note | uspto-grants-2015_02 |