HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetoxyacetyl chloride → acetic acid 2-{4-[2-(2-{5-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3 Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrol-3-yl}-acetylamino)-ethyl]-piperazin-1-yl}-2-oxo-ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetoxyacetyl chloride | HCID 26297 | — |
| Reactant | 2-{5-[5-(2,6-Dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrol-3-yl}-N-(2-piperazin-1-yl-ethyl)-acetamide | HCID 59077555 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | acetic acid 2-{4-[2-(2-{5-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3 Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrol-3-yl}-acetylamino)-ethyl]-piperazin-1-yl}-2-oxo-ethyl ester | HCID 69995976 | 86.4% |
Reaction Steps
A mixture of 2-{5-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrol-3-yl}-N-(2-piperazin-1-yl-ethyl)-acetamide (300 mg, 0.475 mmol), acetoxyacetyl chloride (97 mg, 1.5 eq.) and TEA (0.5 mL) in DCM (10 mL) was stirred at rt for overnight. The precipitate was collected by vacuum filtration, washed with water and methanol to give 300 mg of acetic acid 2-{4-[2-(2-{5-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrol-3-yl}-acetylamino)-ethyl]-piperazin-1-yl}-2-oxo-ethyl ester as a red solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06599902B2 |
| Source dataset | uspto-grants-2003_07 |
| ORD ID | ord-c7e6e3ace35b4249abc6628a4a4244fc |
| Source note | uspto-grants-2003_07 |