HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → HCID 89955016, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 3,3-Difluoroazetidine hydrochloride | HCID 2758247 | — |
| Reactant | HCID 86710128 | HCID 86710128 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 89955016 | HCID 89955016 | 93.5% |
Reaction Steps
6-Chloro-7-cyano-2-isopropylimidazo[1,2-a]pyridine-3-sulfonylchloride (1.00 g, 3.14 mmol) obtained in step 3 was dissolved in acetonitrile (10 mL), and the solution was stirred at room temperature for 1.25 hours after adding 3,3-difluoroazetidinehydrochloride (611 mg, 4.71 mmol) and triethylamine (1.31 mL, 9.43 mmol). A saturated sodium hydrogen carbonate aqueous solution was added to the reaction mixture. The precipitated crystals were collected by filteration, and washed with water. The resulting crude product was purified by silica gel column chromatography (heptane/ethyl acetate=80/20→50/50) to give 6-chloro-3-(3,3-difluoroazetidin-1-ylsulfonyl)-2-isopropylimidazo[1,2-a]pyridine-7-carbonitrile (1.10 g, yield 93%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09000186B2 |
| Source dataset | uspto-grants-2015_04 |
| ORD ID | ord-72ae0950cf95483eb1fefe370b101c30 |
| Source note | uspto-grants-2015_04 |