HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → METHYL[[8-CHLORO-6,11-DIHYDRO-11-[1-[1-OXO-2-(3-PYRIDINYL)ETHYL]-4-PIPERIDINYLIDENE]-5H-BENZO[5,6]CYCLOHEPTA[1,2-b]PYRIDIN-4-YL]THIO]ACETATE
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Methyl Thioglycolate | HCID 16907 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 4-[4,8-Dichloro-5,6-Dihydro-11H-Benzo[5,6]Cyclohepta[1,2-b]Pyridin-11-Ylidene]-1-(3-Pyridinylacetyl)-Piperidine | HCID 22621955 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | METHYL[[8-CHLORO-6,11-DIHYDRO-11-[1-[1-OXO-2-(3-PYRIDINYL)ETHYL]-4-PIPERIDINYLIDENE]-5H-BENZO[5,6]CYCLOHEPTA[1,2-b]PYRIDIN-4-YL]THIO]ACETATE | HCID 18715443 | 15% |
Reaction Steps
A mixture of the title compound from Example 250 (0.26 grams), sodium hydride (0.08 grams, 60% in mineral oil), methyl thioglycolate (0.19 mL) and anhydrous DMF (15 mL) was stirred while being irradiated with a 200 W lamp for 16 hours. The mixture was diluted with MeOH, concentrated in vacuo, diluted with CH2Cl2 and water, and washed with 1N aqueous NaOH and brine. The organic phase was dried over anhydrous MgSO4 and concentrated in vacuo and the residue purified by preparative plate chromatography (silica gel) using 3% MeOH—CH2Cl2 to afford the title compound (0.05 grams, 15%, MH+ 534).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06242458B1 |
| Source dataset | uspto-grants-2001_06 |
| ORD ID | ord-513fce4a5d6b4d738ad6493b9e76c81a |
| Source note | uspto-grants-2001_06 |