Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Citric Acid | HCID 311 | — |
| Reactant | Methanesulfonamide | HCID 72879 | — |
| Reactant | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| Reactant | HCID 67211673 | HCID 67211673 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 67210606 | HCID 67210606 | 41.5% |
Reaction Steps
(E)-[2-(2-Propylbenzimidazol-1-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetic acid (60 mg, 0.14 mmol) obtained in Example 2 was dissolved in DMF (0.6 mL), N,N′-carbonyldiimidazole (92 mg, 0.57 mmol) was added, and the mixture was stirred at room temperature for 1 hr. Methanesulfonamide (68 mg, 0.71 mmol) and DBU (106 μL, 0.71 mmol) were added to the reaction mixture, and the mixture was stirred at 80° C. for 2 hr. Water and 5% aqueous citric acid solution were added to the mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Ethyl acetate was added to the residue, and the mixture was filtered to give the title compound (compound 12) (29 mg, 41%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08486980B2 |
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| Source dataset | uspto-grants-2013_07 |
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| ORD ID | ord-3617633d8d81494285097fb367ce9849 |
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| Source note | uspto-grants-2013_07 |
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