HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → HCID 118158016, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 8-Azabicyclo[3.2.1]octan-3-one hydrochloride | HCID 13091218 | — |
| Reactant | N-benzyl-4-((3-chloro-4-methoxybenzyl)amino)-2-(methylsulfinyl)pyrimidine-5-formamide | HCID 118157494 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 118158016 | HCID 118158016 | 19.8% |
Reaction Steps
In DCM were dissolved N-benzyl-4-((3-chloro-4-methoxybenzyl)amino)-2-(methyl sulfinyl)pyrimidine-5-formamide (222 mg, 0.5 mmol) and DIEA (0.25 mL, 1.35 mmol). 3-oxo-8-azabicyclo[3.2.1] octane hydrochloride salt (90 mg, 0.6 mmol) was dissolved in THF and added to the reaction mixture at 0° C. The reaction was conducted at ambient temperature, followed by addition of water and extraction with ethyl acetate. The organic phase was washed sequentially with water and brine, and dried over sodium sulfate. The solvent was removed by rotary evaporation. Purification was performed by silica gel column chromatography (petroleum ether/ethyl acetate=1/1) to give a white solid (50 mg, 19% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09359371B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-8bb4970c3aa94f46a7d4c2edc5f6fc0a |
| Source note | uspto-grants-2016_06 |