HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Hydroxybenzotriazole → 3-ethylsulfanyl-N-methyl-5-trifluoromethyl-N-(5-trifluoromethylpyridin-2-yl)picolinamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | N-Methyl-5-(trifluoromethyl)pyridin-2-amine | HCID 18526206 | — |
| Reactant | 3-Ethylsulfanyl-5-trifluoromethylpicolinic acid | HCID 71246893 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Product | 3-ethylsulfanyl-N-methyl-5-trifluoromethyl-N-(5-trifluoromethylpyridin-2-yl)picolinamide | HCID 118113423 | 22.1% |
Reaction Steps
A mixture of 0.35 g of 2-methylamino-5-trifluoromethylpyridine, 0.50 g of 3-ethylsulfanyl-5-trifluoromethylpicolinic acid, 0.46 g of EDCI hydrochloride, 0.02 g of HOBt and 3 mL of pyridine was stirred at room temperature for 3 hours. A saturated aqueous sodium bicarbonate solution was poured to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure, and the resulting residue was applied to a silica gel column chromatography to obtain 0.18 g of 3-ethylsulfanyl-N-methyl-5-trifluoromethyl-N-(5-trifluoromethylpyridin-2-yl)picolinamide (hereinafter, referred to as Compound of Present Invention 24).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09185910B2 |
| Source dataset | uspto-grants-2015_11 |
| ORD ID | ord-458a5450666b49328c77ae9d77320c27 |
| Source note | uspto-grants-2015_11 |