Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-Cyano-3-(2,4-dimethoxybenzyl)-5-(3-indolyl)-1-(1-methyl-3-indolyl)-2,3-dihydroimidazol-2-one | HCID 18320729 | — |
| Product | HCID 69952117 | HCID 69952117 | 54% |
Reaction Steps
Two portions of totally 0.72 g (2.33 mmol) of 1(R)-O-Methanesulfonyl-3(S)-phthalimido-cyclopentane and two portions of totally 1.33 g (4.05 mmol) of cesium carbonate were added within 1.5 hours, to a stirred solution of 0.26 g (0.51 mmol) 4-cyano-3-(2,4-dimethoxybenzyl)-5-(3-indolyl)-1-(1-methyl-3-indolyl)-2,3-dihydroimidazol-2-one in 3 ml of dry DMF at 70° C. After an additional 2 hours, the reaction mixture was cooled to room temperature and partitioned between ethyl acetate and saturated brine. The aqeous phase was back-extracted with ethyl acetate and the combined organic extracts washed three times with saturated brine, dried over Na2SO4 and concentrated. The residue was purified by chromatography on SiO2 (EtOAc-heptane, 3:2). The fractions containing the desired product were combined and crystallized (chloroform:ether) to give the sub-title compound (0.20 g, 54%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06346625B1 |
|---|
| Source dataset | uspto-grants-2002_02 |
|---|
| ORD ID | ord-fabd5a304e664462824c0548175737dd |
|---|
| Source note | uspto-grants-2002_02 |
|---|