HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → Tert-butyl (3-((6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinamido)methyl)pyridin-2-yl)methylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| 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 | — |
| Reactant | tert-butyl N-{[3-(aminomethyl)pyridin-2-yl]methyl}carbamate | HCID 57542432 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Tert-butyl (3-((6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinamido)methyl)pyridin-2-yl)methylcarbamate | HCID 57542397 | 57% |
Reaction Steps
To a mixture of 6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinic acid (0.60 g, 1.66 mmol) in DMF (3 mL) was added DIEA (0.329 mL, 2.53 mmol), HBTU (0.756 g, 2.00 mmol), then tert-butyl (3-(aminomethyl)pyridin-2-yl)methylcarbamate (0.473 g, 2.11 mmol). The reaction mixture was stirred at room temperature for 1 hr. The crude mixture was purified on RP-HPLC using a mixture of acetonitrile and H2O to give tert-butyl (3-((6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinamido)methyl)pyridin-2-yl)methylcarbamate as a pale yellow solid (545 mg, 57%). LRMS (M+H+) m/z 581.3.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07932270B2 |
| Source dataset | uspto-grants-2011_04 |
| ORD ID | ord-daba292d518c455f8b9d9c6728f30ac4 |
| Source note | uspto-grants-2011_04 |