Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-Methylbenzoyl Chloride | HCID 13405 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 66887136 | HCID 66887136 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 66886848 | HCID 66886848 | 54% |
Reaction Steps
To a solution of 2-{3-[1-(1-benzyl-5-methyl-1H-benzimidazol-2-yl)-2-methyl-propylamino]-propyl}-isoindole-1,3-dione (0.56 mmol) and triethylamine (0.58 mL, 3.36 mmol) in DCM (3 mL) at 0° C., was added p-toluoyl chloride (0.38 mL, 2.8 mmol). The reaction mixture was stirred at 0° C. for 30 min. Ethyl acetate and saturated sodium bicarbonate were added. The mixture was extracted with ethyl acetate. The organic layers was combined, dried over MgSO4, filtered, and the filtrate was concentrated in vacuo. The crude material was purified by flash chromatography to give N-[1-(1-benzyl-5-methyl-1H-benzimidazol-2-yl)-2-methyl-propyl]-N-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propyl]-4-methyl-benzamide (181 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07608723B2 |
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| Source dataset | uspto-grants-2009_10 |
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| ORD ID | ord-7637e96b4df347a3bd83d1a82ef85fd4 |
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| Source note | uspto-grants-2009_10 |
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