HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dichloromethane → 4-(piperidin-4-yl)-3,4-dihydropyrrolo[4,3,2-de][2,6]naphthyridin-5(1H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | tert-Butyl 4-(5-oxopyrrolo[4,3,2-de][2,6]naphthyridin-4(1H,3H,5H)-yl)piperidine-1-carboxylate | HCID 49841655 | — |
| Solvent | Trifluoroacetic acid | HCID 6422 | — |
| Product | 4-(piperidin-4-yl)-3,4-dihydropyrrolo[4,3,2-de][2,6]naphthyridin-5(1H)-one | HCID 49841656 | 91.8% |
Reaction Steps
tert-Butyl 4-(5-oxopyrrolo[4,3,2-de][2,6]naphthyridin-4(1H,3H,5H)-yl)piperidine-1-carboxylate (18 mg, 0.051 mmol) was dissolved in TFA (1 mL) and DCM (2 mL) and allowed to stir at room temperature for 15 min. The mixture was concentrated in vacuo and purified via preparative HPLC 10% to 40% B in A and gave 12 mg of the title compound as its TFA salt. 1H NMR (400 MHz, CD3OD) δ 8.71-8.72 (s, 1H), 8.42 (d, 1H, J=8.4 Hz), 7.62 (s, 1H), 7.48-7.49 (m, 2H), 5.02 (s, 1H), 4.69-4.75 (m, 2H), 3.58-3.61 (m, 2H), 3.19-3.26 (m, 2H), 2.33-2.39 (m, 2H), 2.10-2.15 (m, 2H). [M+H] found 257.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08420816B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-cf0ca336090a4e98aa2d3d76e4d1bb43 |
| Source note | uspto-grants-2013_04 |