Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Dimethylamine, hydrochloride | HCID 10473 | — |
| Reactant | 2-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborate | HCID 9857522 | — |
| Reactant | HCID 68787018 | HCID 68787018 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 59636766 | HCID 59636766 | 68.3% |
Reaction Steps
Lithium 7-(4-benzylpiperazin-1-yl)-5-fluorobenzofuran-2-carboxylate (0.86 g, 2.38 mmol) was dissolved in dry dimethylformamide (10 mL), 2-succinimido-1,1,3,3-tetramethyluronium tetrafluoroborate (TSTU) (0.93 g, 3.10 mmol) was added followed by triethylamine (1.16 mL, 8.34 mmol). The reaction was stirred for 20 min then dimethylamine hydrochloride (0.78 g, 9.54 mmol) was added. The reaction was stirred at rt over night. The solvent was evaporated and water and dichloromethane were added. The layers were separated. The aqueous phase was extracted with dichloromethane (3×). The combined organic phases were washed with water (3×) and brine, dried (Na2SO4), filtered and evaporated. The crude was purified by flash chromatography (SiO2; DCM/MeOH; 97/3) to give 0.62 g (68%) of the product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08367676B2 |
|---|
| Source dataset | uspto-grants-2013_02 |
|---|
| ORD ID | ord-abfaa913c96b45b2ba989f3d931d7e77 |
|---|
| Source note | uspto-grants-2013_02 |
|---|