HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Hydroxybenzotriazole → Tert-butyl 4-(2-((6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinamido)methyl)pyrrolidin-1-yl)-4-oxobutylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 4-(((Tert-butoxy)carbonyl)amino)butanoic acid | HCID 294894 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Reactant | HCID 67101158 | HCID 67101158 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Tert-butyl 4-(2-((6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinamido)methyl)pyrrolidin-1-yl)-4-oxobutylcarbamate | HCID 57542726 | 65% |
Reaction Steps
To a mixture of 6-(2-cyanophenyl)-2-(3-fluorophenethylamino)-N-(pyrrolidin-2-ylmethyl)nicotinamide hydrochloride (95 mg, 0.2 mmol), 4-(tert-butoxycarbonylamino)butanoic acid (61 mg, 0.3 mmol), HOBT (41 mg, 0.3 mmol), and HBTU (114 mg, 0.3 mmol) were added DMF (1.0 mL) and DIEA (0.1 mL, 0.6 mmol). The reaction mixture was stirred at r.t. for 1 h. LC/MS indicated the reaction was complete. The reaction mixture was then filtered and the filtrate was purified on RP-HPLC using a mixture of acetonitrile and water to give tert-butyl 4-(2-((6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinamido)methyl)pyrrolidin-1-yl)-4-oxobutylcarbamate (81.2 mg, 65%). LRMS (M+H+) m/z 629.2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07932270B2 |
| Source dataset | uspto-grants-2011_04 |
| ORD ID | ord-07140d22ddf74e77983fa96bd6a68676 |
| Source note | uspto-grants-2011_04 |