HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Hydroxybenzotriazole → N-(Tetrahydro-2H-pyran-4-yl)-N-[3-(trifluoromethoxy)benzyl]imidazo[1,2-a]pyridine-2-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Imidazo[1,2-a]pyridine-2-carboxylic acid | HCID 2062168 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | N-[3-(Trifluoromethoxy)benzyl]tetrahydro-2H-pyran-4-amine | HCID 58049381 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | N-(Tetrahydro-2H-pyran-4-yl)-N-[3-(trifluoromethoxy)benzyl]imidazo[1,2-a]pyridine-2-carboxamide | HCID 58049370 | 77.6% |
Reaction Steps
N-[3-(Trifluoromethoxy)benzyl]tetrahydro-2H-pyran-4-amine (242 mg), imidazo[1,2-a]pyridine-2-carboxylic acid (194 mg), EDC.HCl (199 mg), HOBt (138 mg), dimethylformamide (5 mL) and triethylamine (0.33 mL) was stirred overnight at room temperature. The solvents were distilled off under reduced pressure and following extraction with ethyl acetate, the extract was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated saline, and dried over anhydrous magnesium sulfate. The desiccant was filtered off and, thereafter, the solvents were concentrated. The residue was purified by column chromatography (NH silica gel cartridge; ethyl acetate) to give the titled compound (286 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08623898B2 |
| Source dataset | uspto-grants-2014_01 |
| ORD ID | ord-475c298679004f1aad31a27ea279918a |
| Source note | uspto-grants-2014_01 |