Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | HCID 66795539 | HCID 66795539 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 86663312 | HCID 86663312 | 97.7% |
Reaction Steps
Mesyl chloride (280 μL; 3.6 mmol) was added to a solution of 2-(4-(3-(2,5-difluorophenyl)-1,2,4-oxadiazol-5-yl)-5-phenyl-1H-pyrazol-1-yl)ethanol (663 mg; 1.8 mmol), obtained from step 1, and triethylamine (502 μL; 3.6 mmol) in dry DCM (5 mL) at 0° C. The tube was sealed and allowed to warm to room temperature overnight. The mixture was washed with saturated aqueous sodium hydrogen carbonate and the organic fraction passed through a hydrophobic frit and the solvent removed in vacuo to give the title compound as a pale yellow solid (785 mg; 97%). 1H NMR (CDCl3, 400 MHz) δ 8.31 (1 H, s), 7.69-7.64 (1 H, m), 7.59-7.81 (3 H, m), 7.50-7.45 (2H, m), 7.21-7.10 (2 H, m), 4.64 (2 H, t, J=5.2 Hz), 4.38 (2 H, t, J=5.2 Hz), 2.90 (3 H, s). LC/MS: 447 (M+H)+. HPLC (Method A) Rt=3.69 min (Purity: 99.4%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08802663B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-dcf615b6bf054d4bb4d05b2e9e9eeedf |
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| Source note | uspto-grants-2014_08 |
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