HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyridine → Chloro-pyridine-3-sulfonic acid (4-fluoro-phenyl)-isobutyl-amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 2-Chloro-5-pyridinesulfonyl chloride | HCID 2792792 | — |
| Reactant | 4-Fluoro-N-(2-methylpropyl)aniline | HCID 18543711 | — |
| Solvent | Water | HCID 962 | — |
| Product | Chloro-pyridine-3-sulfonic acid (4-fluoro-phenyl)-isobutyl-amide | HCID 86721872 | 80% |
Reaction Steps
To a solution of (4-fluoro-phenyl)-isobutyl-amine (250 mg, 1.5 mmol) in DCM (5 mL) was added pyridine (242 μL, 3.0 mmol) followed by 6-chloropyridine-3-sulfonylchloride (379 mg, 1.8 mmol) and the reaction was stirred at room temperature for 2 hours. Water and saturated NaHCO3 were added and then extracted with DCM, filtered through a phase separator, concentrated then purified by silica gel column chromatography (0-20% EtOAC in cyclohexane) to give chloro-pyridine-3-sulfonic acid (4-fluoro-phenyl)-isobutyl-amide (411 mg, 80%) LCMS (m/z, Method A) ES+ 343 [M+1]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09382222B2 |
| Source dataset | uspto-grants-2016_07 |
| ORD ID | ord-e62a2f49510444bd81eb0e87bd98fd34 |
| Source note | uspto-grants-2016_07 |