HuagongsheHuagongshe Chemistry Print Report · For research reference only
Propionic Acid → 4-(4-ethyl-1-propionylpiperidin-4-yl)-3,4-dihydropyrrolo[4,3,2-de][2,6]naphthyridin-5(1H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Propionic Acid | HCID 1032 | — |
| 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 | HCID 49841776 | HCID 49841776 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 4-(4-ethyl-1-propionylpiperidin-4-yl)-3,4-dihydropyrrolo[4,3,2-de][2,6]naphthyridin-5(1H)-one | HCID 49841901 | 32.2% |
Reaction Steps
4-(4-Ethylpiperidin-4-yl)-3,4-dihydropyrrolo[4,3,2-de][2,6]naphthyridin-5(1H)-one (12 mg, 0.042 mmol), propionic acid (4 mg, 0.055 mmol), 4-dimethylaminopyridine (10 mg, 0.084 mmol), and HATU (32 mg, 0.084 mmol) were dissolved in DMF (3 mL) at room temperature and allowed to stir for 3 h. The solution was concentrated in vacuo and purified via preparative HPLC 10% to 40% B in A and gave 4.6 mg of the title compound as its TFA salt. 1H NMR (400 MHz, CD3OD) δ 7.58 (m, 1H), 7.41 (m, 1H), 5.12 (s, 2H), 3.70-3.74 (m, 1H), 3.59-3.63 (m, 3H), 2.58-2.61 (m, 1H), 2.41-2.43 (m, 3H), 2.21-2.30 (m, 4H), 1.11 (t, 3H, J=7.6 Hz), 0.94 (t, 3H, J=7.6 Hz). [M+H] found 341.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08420816B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-6da7bf4e788d4142a567838e3e189efc |
| Source note | uspto-grants-2013_04 |