HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Hydroxybenzotriazole → (R)-tert-butyl 2-((6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinamido)methyl)pyrrolidine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | tert-butyl (2R)-2-(aminomethyl)pyrrolidine-1-carboxylate | HCID 1512534 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Reactant | 6-(2-Cyanophenyl)-2-(3-fluorophenethylamino)nicotinic acid | HCID 57542304 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (R)-tert-butyl 2-((6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinamido)methyl)pyrrolidine-1-carboxylate | HCID 57543030 | 91% |
Reaction Steps
To a mixture of 6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinic acid (510 mg, 1.41 mmol), (R)-tert-butyl 2-(aminomethyl)pyrrolidine-1-carboxylate (424 mg, 2.11 mmol), HOBT (285 mg, 2.11 mmol), and HBTU (800 mg, 2.11 mg) in RB flask was added DMF and the mixture was stirred at r.t. for 1 h. LC/MS indicated the reaction was complete and the mixture was filtered and purified on RP-HPLC using a mixture of acetonitrile and water to give (R)-tert-butyl 2-((6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinamido)methyl)pyrrolidine-1-carboxylate (695.1 mg, 91%). LRMS (M+H+) m/z 544.2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07932270B2 |
| Source dataset | uspto-grants-2011_04 |
| ORD ID | ord-c4de64ba5339450c98dbe1e830d07f53 |
| Source note | uspto-grants-2011_04 |