Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 1,1'-Carbonyldiimidazole | HCID 68263 | — |
| Reactant | Methanesulfonamide | HCID 72879 | — |
| Reactant | Diazabicycloundecane | HCID 57346892 | — |
| Reactant | HCID 70100356 | HCID 70100356 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 86756090 | HCID 86756090 | 92.7% |
Reaction Steps
A solution of {{2-{5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-6-fluoro-1,2-benzisoxazol-3-yl}-p-tolyl}oxy}acetic acid (1.54 g, 0.00312 mol) in tetrahydrofuran is added dropwise to a suspension of 1,1'-carbonyldiimidazole (1.06 g, 0.00655 mol) in tetrahydrofuran. The resultant mixture is stirred 1.5 hours and cooled to room temperature. A mixture of methanesulfonamide (0.594 g, 0.00624 mol), diazabicycloundecane (1.09 g, 0.00702 mol) and tetrahydrofuran is added dropwise. The resultant mixture is stirred overnight at room temperature and poured into 10% hydrochloric acid. The resultant white solid is filtered and dried to give the title compound (1.65 g, 91.6%, mp 123-125° C.) which is identified by NMR spectral analysis.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06156700 |
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| Source dataset | uspto-grants-2000_12 |
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| ORD ID | ord-4febe38b54ea46c78e96bedd1d00501d |
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| Source note | uspto-grants-2000_12 |
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