HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → 5-{3-[4-Trifluoromethyl-6-(6-trifluoromethyl-pyridin-3-yl)-pyrimidin-2-yl]-phenyl}-thiophene-2-sulfonic acid amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | N-tert-Butyl-5-{3-[4-trifluoromethyl-6-(6-trifluoromethyl-pyridin-3-yl)-pyrimidin-2-yl]-phenyl}-thiophene-2-sulfonic acid amide | HCID 86624637 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 5-{3-[4-Trifluoromethyl-6-(6-trifluoromethyl-pyridin-3-yl)-pyrimidin-2-yl]-phenyl}-thiophene-2-sulfonic acid amide | HCID 25096946 | 49.1% |
Reaction Steps
To a cooled and stirred solution of N-tert-butyl-5-{3-[4-trifluoromethyl-6-(6-trifluoromethyl-pyridin-3-yl)-pyrimidin-2-yl]-phenyl}-thiophene-2-sulfonic acid amide (0.45 g) in dichloromethane (6 ml) was added TFA (6 ml) and the reaction mixture was allowed to stir at room temperature for 15 h. The mixture was evaporated to dryness, poured into 2N Na2CO3 solution (25 ml) and extracted with ethyl acetate (3×50 ml). The combined organic layers were washed with brine (50 ml), dried (MgSO4) and evaporated. Further purification by flash chromatography on silica gel (ethyl acetate/heptane) and crystallization (ethyl acetate/heptane) yielded the title compound as a light yellow solid (0.2 g, 38%). MS (ISP) 531.0 [(M+H)+]; mp 250.5° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08012986B2 |
| Source dataset | uspto-grants-2011_09 |
| ORD ID | ord-0d4ac17df72c4912ba0b5985dc600699 |
| Source note | uspto-grants-2011_09 |