HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 3-{(3R)-3-[(9-fluoro-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridin-6-yl)amino]piperidin-1-yl}-3-oxopropanenitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Cyanoacetic acid | HCID 9740 | — |
| 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 | (3R)-3-[(9-fluoro-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridin-6-yl)amino]piperidinium chloride | HCID 67416365 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 3-{(3R)-3-[(9-fluoro-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridin-6-yl)amino]piperidin-1-yl}-3-oxopropanenitrile | HCID 59375373 | — |
Reaction Steps
To a solution of (3R)-3-[(9-fluoro-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridin-6-yl)amino]piperidinium chloride (40 mg, 0.09 mmol) in DMF (2 mL) were added triethylamine (0.13 mL, 0.94 mmol), HATU (0-(7-Azabenzotriazol-1-yl)-N,N,N,N-tetramethyluronium hexafluorophosphate) (36 mg, 0.094 mmol), and cyanoacetic acid (40 mg, 0.47 mmol). The solution was stirred at room temperature overnight. The crude solution was filtered and purified by reverse phase HPLC. LRMS (ESI) calc'd for (C20H19FN5O2) [M+H]+, 380.2; found 380.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08329722B2 |
| Source dataset | uspto-grants-2012_12 |
| ORD ID | ord-aff70e038aba467f9efc2a57f61b5e2b |
| Source note | uspto-grants-2012_12 |