HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanesulfonyl chloride → (+/-)-6-Bromo-4-((4,4-dimethyl-1-(methylsulfonyl)pyrrolidin-3-yl)amino)pyrrolo[1,2-b]pyridazine-3-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 6-Bromo-4-((4,4-dimethylpyrrolidin-3-yl)amino)pyrrolo[1,2-b]pyridazine-3-carboxamide hydroiodide | HCID 68292078 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (+/-)-6-Bromo-4-((4,4-dimethyl-1-(methylsulfonyl)pyrrolidin-3-yl)amino)pyrrolo[1,2-b]pyridazine-3-carboxamide | HCID 68350406 | 86% |
Reaction Steps
A suspension of 6-bromo-4-((4,4-dimethylpyrrolidin-3-yl)amino)pyrrolo[1,2-b]pyridazine-3-carboxamide hydroiodide (97 mg, 0.25 mmol) in DCM (3 mL), was added DIPEA (0.16 mL, 0.87 mmol) and methanesulfonyl chloride (0.04 mL, 0.5 mmol). The mixture was stirred at rt overnight. The reaction was quenched with water, extracted by dichloromethane, washed with hydrochloride (0.5N), aq. sodium bicarbonate and brine. The organic layer was dried over sodium sulfate and concentrated. The residue was triturated in ether then filtered to give (+/−)-6-bromo-4-(4,4-dimethyl-1-(methylsulfonyl)pyrrolidin-3-ylamino)pyrrolo[1,2-b]pyridazine-3-carboxamide (92 mg, 86%). MS (ES+) m/z: 431.99 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08987268B2 |
| Source dataset | uspto-grants-2015_03 |
| ORD ID | ord-8a610d43c7b64b958838274a461cba64 |
| Source note | uspto-grants-2015_03 |