HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Methylimidazole → Tert-butyl 4-(3-(8-(6-(2-methylpyrrolidin-1-yl)pyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzamido)benzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Methylimidazole | HCID 1390 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | Benzoic acid, 4-amino-, 1,1-dimethylethyl ester | HCID 233272 | — |
| Reactant | 3-(8-(6-(2-Methylpyrrolidin-1-yl)pyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzoic acid | HCID 71525520 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Tert-butyl 4-(3-(8-(6-(2-methylpyrrolidin-1-yl)pyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzamido)benzoate | HCID 89522698 | 61% |
Reaction Steps
A mixture of 3-(8-(6-(2-Methylpyrrolidin-1-yl)pyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzoic acid (49 mg, 0.12 mmol), tert-butyl 4-aminobenzoate (23 mg, 0.12 mmol), EDCI (92 mg, 0.48 mmol), N-methyl-imidazole (40 mg, 0.48 mmol) and dichloromethane (3 mL) was stirred at room temperature for 16 h. The solution was concentrated in vacuo and the residue was purified by chromatography (silica gel, 200-300 mesh, CH2Cl2:MeOH=40:1˜100:1) to give tert-butyl 4-(3-(8-(6-(2-methylpyrrolidin-1-yl)pyridin-2-ylamino)imidazo[1,2-b]pyridazin-6-yl)benzamido)benzoate (43 mg, 61%) as a yellow oil. [M+H]+, 590.2, tR=2.283 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09169259B2 |
| Source dataset | uspto-grants-2015_10 |
| ORD ID | ord-2f2d10b9deee43eaa728614c24cb6877 |
| Source note | uspto-grants-2015_10 |