HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → 1-(2-(4-aminopiperidin-1-yl)ethyl)-7-cyano-1,5-naphthyridin-2(1H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | tert-butyl (1-(2-(7-cyano-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate | HCID 71248370 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Ammonia | HCID 222 | — |
| Product | 1-(2-(4-aminopiperidin-1-yl)ethyl)-7-cyano-1,5-naphthyridin-2(1H)-one | HCID 68816597 | 139.7% |
Reaction Steps
To a solution of 1,1-dimethylethyl {1-[2-(7-cyano-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl]-4-piperidinyl}carbamate (0.411 g, 1.03 mmol) in DCM (16 ml) was added TFA (9 ml) and the reaction stirred at rt for 1 h. The solution was evaporated, dissolved in MeOH and passed through a column of Amberlyst A21 basic resin. The fractions containing the desired product were evaporated and the residue was subjected to column chromatography on silica gel using a DCM:MeOH:aq NH3 gradient to provide the desired compound (0.214 g, 70%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08071592B2 |
| Source dataset | uspto-grants-2011_12 |
| ORD ID | ord-4c15af5bd9174126808a128703f5c241 |
| Source note | uspto-grants-2011_12 |