HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dichloroethane → 3-[1-(4-{(s)-2-[(Cyclopropylmethyl-amino)-methyl]-pyrrolidine-1-carbonyl}-3,5-dimethyl-1h-pyrrol-2-yl)-meth-(z)-ylidene]-4-(3-fluoro-phenyl)-1,3-dihydro-indol-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dichloroethane | HCID 11 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Cyclopropylmethyl-(s)-1-pyrrolidin-2-ylmethyl-amine | HCID 69741373 | — |
| Reactant | 5-[4-(3-Fluoro-phenyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid | HCID 69741386 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 3-[1-(4-{(s)-2-[(Cyclopropylmethyl-amino)-methyl]-pyrrolidine-1-carbonyl}-3,5-dimethyl-1h-pyrrol-2-yl)-meth-(z)-ylidene]-4-(3-fluoro-phenyl)-1,3-dihydro-indol-2-one | HCID 59989643 | — |
Reaction Steps
To a solution of 5-[4-(3-fluoro-phenyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (70 mg, 0.185 mmol), EDC (70 mg, 0.37 mmol), HOBt (26 mg, 0.19 mmol) in DMF (4 mL) was added TEA (0.08 mL) and cyclopropylmethyl-(S)-1-pyrrolidin-2-ylmethyl-amine (0.05 mL, 0.37 mmol). The mixture was stirred at rt for 20 hours. The reaction was diluted with DCM, washed with water, NaHCO3, dried and concentrated. The residue was purified on a silica gel column to give the titled compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06677368B2 |
| Source dataset | uspto-grants-2004_01 |
| ORD ID | ord-54af316cf8a645caa8e94b7e2fa8a9c1 |
| Source note | uspto-grants-2004_01 |