HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 5-chloro-4-(5-chloro-6-(3,3-difluoropyrrolidin-1-yl)pyridin-3-yloxy)-2-fluoro-N-(methylsulfonyl)benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3,3-Difluoropyrrolidine hydrochloride | HCID 24903482 | — |
| Reactant | 5-Chloro-4-[(5-chloro-6-fluoropyridin-3-yl)oxy]-2-fluoro-N-(methylsulfonyl)benzamide | HCID 58042437 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | 5-chloro-4-(5-chloro-6-(3,3-difluoropyrrolidin-1-yl)pyridin-3-yloxy)-2-fluoro-N-(methylsulfonyl)benzamide | HCID 58042420 | — |
Reaction Steps
Triethylamine (0.21 mL, 1.51 mmol) was added to a mixture of 5-chloro-4-[5-chloro-6-fluoropyridin-3-yl)oxy]-2-fluoro-N-(methylsulfonyl)benzamide (Example 19, 150 mg, 0.38 mmol) and 3,3-difluoropyrrolidine hydrochloride salt (60 mg, 0.41 mmol), in DMSO (3.8 mL) and the reaction heated at 80° C. for 120 hours. The mixture was diluted to 5 mL by the addition of water and the mixture purified by preparative HPLC. The title compound was obtained as a beige solid (49 mg, 27%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08592629B2 |
| Source dataset | uspto-grants-2013_11 |
| ORD ID | ord-cbf6ff77008b432f9f53e8a1f049e03a |
| Source note | uspto-grants-2013_11 |