HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → {5-Bromo-2-[3-methoxy-4-(2-pyrrolidin-1-ylethoxy)phenylcarbamoyl]thiophen-3-yl}carbamic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733286 | — |
| Reactant | 5-Bromo-3-((tert-butoxycarbonyl)amino)thiophene-2-carboxylic acid | HCID 21975854 | — |
| Reactant | Methoxy-4-(2-pyrrolidin-1-ylethoxy)phenylamine | HCID 86628783 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | {5-Bromo-2-[3-methoxy-4-(2-pyrrolidin-1-ylethoxy)phenylcarbamoyl]thiophen-3-yl}carbamic acid tert-butyl ester | HCID 68940005 | — |
Reaction Steps
TOTU (327.3 mg) and N,N-diisopropylethylamine (122.8 mg) were added to a mixture of 5-bromo-3-tert-butoxycarbonylaminothiophene-2-carboxylic acid (306.1 mg), methoxy-4-(2-pyrrolidin-1-ylethoxy)phenylamine (224.5 mg) in DMF (3.8 mL). The reaction mixture was stirred at room temperature overnight. Ethyl acetate was then added, and the organic phase was washed with 10% strength citric acid and saturated sodium bicarbonate solution. The organic phase was dried over sodium sulfate and concentrated. The product with the molecular weight of 539.11 (C23H30BrN3O5S) was obtained in this way; MS (ESI): 540, 542 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08853208B2 |
| Source dataset | uspto-grants-2014_10 |
| ORD ID | ord-89395a65deee4b49879a47f6c7533cd6 |
| Source note | uspto-grants-2014_10 |