HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 3-(4-(1-aminocyclobutyl)phenyl)-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridine-8-carbonitrile hydrochloride
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | tert-butyl 1-(4-(8-cyano-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutylcarbamate | HCID 68227519 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 3-(4-(1-aminocyclobutyl)phenyl)-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridine-8-carbonitrile hydrochloride | HCID 67067870 | 71% |
Reaction Steps
To a solution of tert-butyl 1-(4-(8-cyano-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutylcarbamate (10 mg, 0.020 mmol) in DCM (2 mL) was added 4M HCl in 1,4-dioxane (1.0 ml). The reaction mixture was stirred at RT for overnight. The solvent was evaporated and the crude product was washed several times with DCM and acetonitrile (3×1 ml). The product was dried to give the title compound as the HCl salt (5 mg, 71%). 1H NMR (500 MHz, CD3OD): δ 8.55 (d, 1H), 8.15 (d, 1H), 7.48-7.18 (m, 9H), 2.75-2.67 (m, 2H), 2.55-2.42 (m, 2H), 2.18-2.09 (m, 1H), 1.88-1.73 (m, 1H). LCMS (Method I): RT=4.39 min, [M+2]+=395.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08546376B2 |
| Source dataset | uspto-grants-2013_10 |
| ORD ID | ord-c562e43e16084cb58d33f0cfb9ec5734 |
| Source note | uspto-grants-2013_10 |