Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | 3,3,3-Trifluoropropionyl chloride | HCID 2783343 | — |
| Reactant | N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-(methyl amino)propanamide | HCID 86700623 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 118023006 | HCID 118023006 | — |
Reaction Steps
A solution of N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-(methyl amino)propanamide (0.070 g, 0.23 mmol) in dry CH2Cl2 (0.76 mL) was cooled to a temperature of about 0° C. under N2. To the solution, DMAP (0.014 g, 0.11 mmol), pyridine (0.028 mL, 0.34 mmol), and 3,3,3-trifluoropropanoyl chloride (0.026 mL, 0.25 mmol) were added sequentially. The reaction was slowly warmed up to room temperature under N2, then stirred at room temperature overnight. The reaction was diluted with water (2 mL) and stirred for five minutes. Layers were separated, and the aqueous layer was extracted with CH2Cl2 (2×2 mL). The combined organic extracts were dried and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 0%-5% MeOH/CH2Cl2 to afford the title compound F102 as a white semi-solid (0.062 g, 63%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09295260B2 |
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| Source dataset | uspto-grants-2016_03 |
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| ORD ID | ord-daf433ebf04b4d089cc27ad89fa12c67 |
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| Source note | uspto-grants-2016_03 |
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