HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → 2-{[(1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl]methoxy}-3-(piperidin-3-yl)-1,5-naphthyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Tert-butyl 3-(2-{[(1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl]methoxy}-1,5-naphthyridin-3-yl)piperidine-1-carboxylate | HCID 71062617 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-{[(1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl]methoxy}-3-(piperidin-3-yl)-1,5-naphthyridine | HCID 117689158 | — |
Reaction Steps
To a solution of tert-butyl 3-(2-{[(1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl]methoxy}-1,5-naphthyridin-3-yl)piperidine-1-carboxylate (RR2) (38 mg, 0.08 mmol) in DCM (3 mL) was added concentrated TFA (0.5 mL, 6.5 mmol). After five minutes, saturated sodium bicarbonate (3 mL) was added and the mixture was extracted with EtOAc (3×15 mL). The combined organics were dried over MgSO4, filtered and concentrated in vacuo to afford the title compound, which was sufficiently pure to use in the subsequent step without further purification. HRMS m/z (M+H) 391.2133 found, 391.2129 required.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08975261B2 |
| Source dataset | uspto-grants-2015_03 |
| ORD ID | ord-c2bf877f1ff74224a7597e095f3f4860 |
| Source note | uspto-grants-2015_03 |