Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Aniline | HCID 6115 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 8-methylimidazo[1,2-a]pyridine-2-carboxylic acid | HCID 2759860 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | HCID 24771608 | HCID 24771608 | 76.9% |
Reaction Steps
1.67 ml of triethylamine, 1.53 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 1.08 g of 1-hydroxybenzotriazole are added to a solution of 0.176 g of 8-methylimidazo[1,2-a]pyridine-2-carboxylic acid in 12 ml of dichloromethane. The reaction mixture is stirred at ambient temperature for 20 minutes. 0.090 ml of aniline is added. The reaction mixture is stirred at ambient temperature for 4 hours. 60 ml of dichloromethane and 30 ml of water are added. After separation by settling, the organic phase is dried over magnesium sulfate, filtered and evaporated to dryness under reduced pressure. After purifying by flash chromatography (silica, eluent dichloromethane/ethyl acetate 98/02 by volume), 0.193 g of 8-methyl-N-phenylimidazo[1,2-a]pyridine-2-carboxamide is obtained in the form of a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08404848B2 |
|---|
| Source dataset | uspto-grants-2013_03 |
|---|
| ORD ID | ord-dabbcb4af0bb4b46850cd61445a14e3f |
|---|
| Source note | uspto-grants-2013_03 |
|---|
