HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 5-({[(4-bromo-2,6-dichlorophenyl)sulfonyl](methyl)amino}methyl)-N-{2-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]ethyl}-N-methylfuran-3-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 5-({[(4-Bromo-2,6-dichlorophenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid | HCID 58393425 | — |
| Reactant | 2-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-N-methylethanamine | HCID 67217191 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 5-({[(4-bromo-2,6-dichlorophenyl)sulfonyl](methyl)amino}methyl)-N-{2-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]ethyl}-N-methylfuran-3-carboxamide | HCID 46175364 | — |
Reaction Steps
To a stirred solution of 5-({[(4-bromo-2,6-dichlorophenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid (54 mg, 0.12 mmol), EDCI (29 mg, 0.15 mmol) and HOBt (20 mg, 0.15 mmol) in DMF (3 mL) was added a solution of 2-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-N-methylethanamine.HCl (29 mg, 0.11 mmol) and DIPEA (0.084 mL, 0.48 mmol) in DMF (2 mL). The reaction was stirred at ambient temperature for 18 h, then diluted with EtOAc. The solution was washed with water, saturated aqueous NaHCO3 and 1:1 saturated brine:water. The organic extracts were dried over MgSO4, and solvent was removed in vacuo. A portion of the crude product was purified using prep method C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08623859B2 |
| Source dataset | uspto-grants-2014_01 |
| ORD ID | ord-868d4065189749e38d4558a0ebe7820e |
| Source note | uspto-grants-2014_01 |