HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 5-(6-Bromo-2-phenyl-imidazo[1,2-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl 5-(chlorocarbonyl)-1-methyl-1H-pyrazole-4-carboxylate | HCID 60136485 | — |
| Reactant | 6-Bromo-2-phenylimidazo[1,2-A]pyridin-7-amine | HCID 67041913 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 5-(6-Bromo-2-phenyl-imidazo[1,2-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester | HCID 67042278 | 23% |
Reaction Steps
A solution of 5-chlorocarbonyl-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (as prepared in Example 14, Step 2, 2.35 g, 10.8 mmol) in dichloromethane (5 ml) was added dropwise over 20 min to a cooled (0° C.) solution of 6-bromo-2-phenyl-imidazo[1,2-a]pyridin-7-ylamine (1.56 g, 5.4 mmol) and triethylamine (877 mg) in dichloromethane (20 ml); the mixture was then stirred for at r.t. (30 min). The mixture was washed (water), and the organic layer was dried (Na2SO4), and evaporated. The title compound (460 mg, 23%) was isolated by filtration over a column of silica gel with dichloromethane as an eluent, and was used without further purification in the next step. MS (m/e)=470.1 [M+H+].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08263584B2 |
| Source dataset | uspto-grants-2012_09 |
| ORD ID | ord-9069bb4f34514aaeb029c69260712784 |
| Source note | uspto-grants-2012_09 |