HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,1'-Carbonyldiimidazole → 2-(4-(4,9-diethoxy-1-oxo-1H-benzo[f]isoindol-2(3H)-yl)phenyl)-N-((4-fluorophenyl)sulfonyl)acetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,1'-Carbonyldiimidazole | HCID 68263 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 4-Fluorobenzenesulfonamide | HCID 120231 | — |
| Reactant | [4-(4,9-diethoxy-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetic acid | HCID 9931112 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-(4-(4,9-diethoxy-1-oxo-1H-benzo[f]isoindol-2(3H)-yl)phenyl)-N-((4-fluorophenyl)sulfonyl)acetamide | HCID 9894082 | 35.3% |
Reaction Steps
To a solution of carbonyldiimidazole (13.2 mg, 0.081 mmol) and [4-(4,9-diethoxy-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetic acid (30 mg, 0.074 mmol) in dichloromethane (2 ml) was added 4-fluorobenzenesulphonamide (14.3 mg, 0.081 mmol) and N,N-diisopropylethylamine (10.5 mg, 0.81 mmol). The mixture was stirred at ambient temperature under an atmosphere of nitrogen overnight. The reaction mixture was diluted with dichloromethane (3 ml) and then washed with 2N hydrochloric acid (5 ml). The organic phase was dried (MgSO4) and then concentrated in vacuo to give a brown gum. The residue was purified using mass directed autopurification to give the title compound as a white solid (14.7 mg, 35.3%). MH+563.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07173047B2 |
| Source dataset | uspto-grants-2007_02 |
| ORD ID | ord-74fcd33b573a41169ca8bf9fead8c9a7 |
| Source note | uspto-grants-2007_02 |