Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | N-Cyclopropyl-N-piperidin-4-yl-3-(trifluoromethyl)benzenesulfonamide | HCID 2773944 | — |
| Reactant | 4-Methoxy-3-(trifluoromethyl)benzyl bromide | HCID 2775302 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 57664572 | HCID 57664572 | 79.8% |
Reaction Steps
N-Cyclopropyl-N-piperidin-4-yl-3-trifluoromethylbenzenesulfonamide (200 mg, 0.57 mmol) was dissolved in DMF (4 mL) and triethylamine (200 μL, 1.43 mmol) added, followed by 4-bromomethyl-1-methoxy-2-trifluoromethyl-benzene (154 mg, 0.57 mmol). The reaction mixture was stirred for 12 hours at 80° C. and then the solvent was evaporated. The residue was purified by flash chromatography to give 244 mg of the title compound 18 as a yellow solid. 1H NMR (CDCl3): δ 8.14-8.11 (m, 1H), 8.07-8.03 (m, 1H), 7.86-7.80 (m, 1H), 7.70-7.64 (m, 1H), 7.50-7.47 (m, 1H), 7.42-7.37 (m, 1H), 6.96-6.91 (m, 1H), 3.93-3.79 (m, 4H), 3.42 (s, 2H), 2.91-2.80 (m, 2H), 2.03-1.85 (m, m, 5H), 1.53-1.44 (m, 2H), 1.02-0.96 (m, 2H), 0.83-0.76 (m, 2H). LC: 100%. MS (EI): m/z 537 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09000174B2 |
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| Source dataset | uspto-grants-2015_04 |
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| ORD ID | ord-5d8e4a735a9d4d538355dd5a83c6e45b |
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| Source note | uspto-grants-2015_04 |
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