HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → HCID 89544959, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | HOAt | HCID 181649 | — |
| Reactant | 1-tert-Butyl 3-ethyl 2,5-dihydro-1H-pyrrole-1,3-dicarboxylate | HCID 53888126 | — |
| Reactant | HCID 89544703 | HCID 89544703 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 89544959 | HCID 89544959 | 85.4% |
Reaction Steps
To (1S)-1-{4-chloro-2-fluoro-3-[(pyridin-3-yl)carbonyl]phenyl}propan-1-amine (0.1 g, 0.3 mmol) (Example 26) in DCM was added 1-tert-butyl 3-ethyl 1H-pyrrole-1,3(2H,5H)-dicarboxylate (0.065, 0.3 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (0.07 mg, 0.36 mmol), 1-hydroxy-7-azabenzotriazole (0.049 g, 0.36 mmol) and triethylamine (0.085 ml, 0.6 mmol), then stirred at ambient for 18 hours. The reaction was diluted with DCM washed with 5% citric acid, sat. sodium bicarbonate then brine. The organic extract was dried (Na2SO4), filtered and concentrated to give 3-{(S)-1-[4-Chloro-2-fluoro-3-(pyridine-3-carbonyl)-phenyl]-propylcarbamoyl}-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester (0.125 g). MS: [M+H]+ 488.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09145354B2 |
| Source dataset | uspto-grants-2015_09 |
| ORD ID | ord-c6c392a8af0d49e4b1ff01150bca9e39 |
| Source note | uspto-grants-2015_09 |