HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-(7-Chloro-1,8-naphthyridin-2-yl)-1-oxo-3-isoindolinyl 1-methyl-4-piperidinecarboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| Reactant | 4-Piperidinecarboxylic acid, 1-methyl-, hydrochloride (1:1) | HCID 2760043 | — |
| Reactant | 3-Chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinone | HCID 14182404 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-(7-Chloro-1,8-naphthyridin-2-yl)-1-oxo-3-isoindolinyl 1-methyl-4-piperidinecarboxylate | HCID 86745622 | 42.7% |
Reaction Steps
Working as in Example 1, but starting with 3-chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinone (9.9 g) in anhydrous dimethylformamide (100 cc), 1methyl-4-piperidinecarboxylic acid hydrochloride (5.4 g) and 1,8-diazabicyclo[5.4.0]undec-7-ene (10.7g), and after the residue obtained has been recrystallized twice successively in ethanol and then in acetonitrile, 2-(7-chloro-1,8-naphthyridin-2-yl)-1-oxo-3-isoindolinyl 1-methyl-4-piperidinecarboxylate (5.6 g), m.p. 136° C. and then 157° C., is obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05102890 |
| Source dataset | uspto-grants-1992_04 |
| ORD ID | ord-fb625c33ca80492e974c024b40f83042 |
| Source note | uspto-grants-1992_04 |