HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → N-[4-(8-Methyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-3-piperidin-1-yl-propionamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1-Piperidinepropanoic acid | HCID 117782 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 4-{8-Methylimidazo[1,2-a]pyridin-2-yl}aniline | HCID 2771077 | — |
| Reactant | 1-Hydroxybenzotriazole hydrate | HCID 2796029 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | N-[4-(8-Methyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-3-piperidin-1-yl-propionamide | HCID 22015607 | 23.9% |
Reaction Steps
To a mixture of the product of Step B (330 mg) and N,N-diisopropylethylamine (0.28 mL) in dichloromethane (3 mL) and N,N-dimethylformamide (1 mL), was added 1-piperidinepropionic acid (256 mg), WSC.HCl (1-Ethyl-3-(3′dimethylaminopropyl)-carbodiimide.HCl) (312 mg), and 1-hydroxybenzotriazole hydrate (220 mg). The solution was stirred at ambient temperature for approximately 18 hours. The mixture was poured into a separatory funnel and washed sequentially with an equal volume of 1 N sodium hydroxide and water. The organic phase was dried over sodium sulfate, decanted and evaporated. The residue was purified via silica gel chromatography (methanol/dichloromethane) to yield the title compound (128 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07087757B2 |
| Source dataset | uspto-grants-2006_08 |
| ORD ID | ord-e9297e9f797943d9b05989f796ddd673 |
| Source note | uspto-grants-2006_08 |