Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tryptamine | HCID 1150 | — |
| Reactant | Sodium Chloride | HCID 5234 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 86683891 | HCID 86683891 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | HCID 86683893 | HCID 86683893 | 43.8% |
Reaction Steps
Potassium carbonate (27 mg) and tryptamine (32 mg) were added to an N-methylpyrrolidone (1 ml) solution containing 6-(1H-1,2,3-benzotriazol-1-yloxy)-2-(3,5-dimethoxyphenylamino)-5-fluoronicotinamide (41 mg), followed by stirring at 90° C. for 7 hours. The reaction mixture was cooled to room temperature, and potassium carbonate (14 mg) and tryptamine (16 mg) were added, followed by stirring at 90° C. for 7 hours. The reaction mixture was cooled to room temperature, and then water, sodium chloride, and ethyl acetate were added. The organic layer was collected and dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel chromatography (chloroform:methanol=10:0 to 20:1), diisopropylether was added, solid matter was collected by filtration, and a light brown solid of 2-(3,5-dimethoxyphenylamino)-5-fluoro-6-(2-(1H-indole-3-yl)ethylamino)nicotinamide (19 mg) was thus obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08772320B2 |
|---|
| Source dataset | uspto-grants-2014_07 |
|---|
| ORD ID | ord-7c62d02fd4c446869a6a238f5955da25 |
|---|
| Source note | uspto-grants-2014_07 |
|---|