Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethyl Sulfide | HCID 1068 | — |
| Reactant | Triphenylphosphine Oxide | HCID 13097 | — |
| Reactant | Trifluoromethanesulfonic anhydride | HCID 67749 | — |
| Reactant | HCID 59135763 | HCID 59135763 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | HCID 59135754 | HCID 59135754 | 11.5% |
Reaction Steps
To a mixture of triphenylphosphine oxide (790 mg) and acetonitrile (15 mL) was added trifluoromethanesulfonic anhydride (238 μL), and the mixture was stirred at 0° C. for 10 min. A solution of N-[2-(benzylthio)-3-morpholinopropyl]-7-[methyl(pyridin-3-ylsulfonyl)amino]-1H-indole-2-carboxamide (410 mg) and dimethylsulfide (52 μL) in acetonitrile (15 mL) and dichloromethane (15 mL) was added to the mixture, and the mixture was stirred at 0° C. for 2 hr. The reaction mixture was diluted with ethyl acetate (100 mL) and saturated brine (100 mL). The organic layer was dried over sodium sulfate, and filtrated, and the filtrate was concentrated. The obtained residue was purified by preparative HPLC to give the title compound (38.3 mg, yield 11%) as a white solid. melting point 234-236° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07652133B2 |
|---|
| Source dataset | uspto-grants-2010_01 |
|---|
| ORD ID | ord-1dd0759d4457421d8d72c0ee1ad6ef69 |
|---|
| Source note | uspto-grants-2010_01 |
|---|