HuagongsheHuagongshe Chemistry Print Report · For research reference only
Indomethacin → HCID 67427091, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Indomethacin | HCID 3715 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | tert-Butyl [2-(2-aminoethoxy)ethyl]carbamate | HCID 12106198 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 67427091 | HCID 67427091 | 78% |
Reaction Steps
tert-Butyl 2-(2-aminoethoxy)ethylcarbamate (150 mg, 0.735 mmol) was then taken up in CH3CN (10 mL) along with indomethacin (263 mg, 0.735 mmol) and EDCI (155 mg, 0.81 mmol). The resulting reaction mixture was stirred at room temperature for 18 h. It was then diluted with EtOAc (20 mL), washed with saturated aqueous NaHCO3, brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (9:1 CH2Cl2/MeOH) to afford 310 mg of tert-butyl 2-(2-(2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetamido)ethoxy)ethylcarbamate (78%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09216224B2 |
| Source dataset | uspto-grants-2015_12 |
| ORD ID | ord-e3a01a9193fe4e6ba5c9ca4521cffef2 |
| Source note | uspto-grants-2015_12 |