HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → (S)-tert-Butyl 4,4-difluoro-2-(2-(phenylcarbamoyl)-1H-pyrrol-1-ylcarbamoyl)pyrrolidine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| 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 | (2S)-1-[(tert-butoxy)carbonyl]-4,4-difluoropyrrolidine-2-carboxylic acid | HCID 22977458 | — |
| Reactant | 1-amino-N-phenyl-1H-pyrrole-2-carboxamide | HCID 70922454 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (S)-tert-Butyl 4,4-difluoro-2-(2-(phenylcarbamoyl)-1H-pyrrol-1-ylcarbamoyl)pyrrolidine-1-carboxylate | HCID 86722022 | 97.5% |
Reaction Steps
1-Amino-N-phenyl-1H-pyrrole-2-carboxamide (500 mg, 2.48 mmol), (S)-1-(tert-butoxycarbonyl)-4,4-difluoropyrrolidine-2-carboxylic acid (687 mg, 2.73 mmol), HATU (1.04 g, 2.73 mmol) and diisopropylethylamine (476 μl, 2.73 mmol) were dissolved in a mixture of 6 mL of dichloromethane and 6 mL of DMF and stirred at room temperature overnight. The dichloromethane was removed under vacuum and 25 mL of water were poured over the remaining solution. A precipitated appeared and the suspension was stirred overnight. The solid was filtered and washed with water to furnish 1.05 g (97% yield) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09340547B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-0120fe6bc5ad437a855a4937b34e73e1 |
| Source note | uspto-grants-2016_05 |