HuagongsheHuagongshe Chemistry Print Report · For research reference only
5-bromo-2-(5-ethoxy-4-methyl-4,5-dihydroisoxazol-3-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide → 5-bromo-N-methyl-2-(4-methylisoxazol-3-yl)-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 5-bromo-2-(5-ethoxy-4-methyl-4,5-dihydroisoxazol-3-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide | HCID 90332421 | — |
| Solvent | Trifluoroacetic acid methylene chloride | HCID 21863450 | — |
| Product | 5-bromo-N-methyl-2-(4-methylisoxazol-3-yl)-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide | HCID 90332479 | 90.4% |
Reaction Steps
A mixture of 5-bromo-2-(5-ethoxy-4-methyl-4,5-dihydroisoxazol-3-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (50 mg, 0.10 mmol) in DCM/TFA (1 mL/2 mL) was stirred at reflux for 16 h. It was washed with water, brine, dried over Na2SO4, and concentrated. The residue was purified by prep-TLC (DCM:MeOH=20:1) to get 5-bromo-N-methyl-2-(4-methylisoxazol-3-yl)-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (40 mg, yield: 88%). 1H-NMR (CDCl3, 400 MHz) δ 9.14 (br s, 1H), 8.84 (s, 1H), 8.39 (s, 1H), 7.76 (s, 1H), 3.35 (s, 3H), 3.10 (s, 3H), 3.04 (d, J=4.8 Hz, 3H), 2.36 (s, 3H). MS (M+H)+: 442/444.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09243002B2 |
| Source dataset | uspto-grants-2016_01 |
| ORD ID | ord-079e266f986e4ca98c71f9b90be4427c |
| Source note | uspto-grants-2016_01 |