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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1668232Generated: October 30, 2026

4-Methylmorpholine → HCID 57505766, compound

https://huagongshe.com/reaction/1668232

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-MethylmorpholineHCID 7972—
ReactantIsobutyl chloroformateHCID 62365—
Reactant2-Butynoic acidHCID 68535—
ReactantSodium BicarbonateHCID 516892—
ReactantN-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamideHCID 57386059—
SolventPyridineHCID 1049—
SolventDimethylformamideHCID 6228—
SolventTetrahydrofuranHCID 8028—
ProductHCID 57505766HCID 5750576673%

Reaction Steps

To a solution of but-2-ynoic acid (61 mg, 0.581 mmol) in tetrahydrofuran (3 mL) were added isobutyl chlorocarbonate (76 μL, 0.581 mmol) and 4-methylmorpholine (80 μL, 0.727 mmol), a solution of N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide (150 mg, 0.484 mmol) in pyridine (1.5 mL)/N,N-dimethylformamide (2 mL) was further added under ice-cooling, and the mixture was stirred at room temperature for 3 hr. Saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate/tetrahydrofuran. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and filtrated. The solvent was evaporated under reduced pressure, and the residue was washed with ethyl acetate to give the title compound (132 mg, 73%) as a pale-orange powder.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08044049B2
Source datasetuspto-grants-2011_10
ORD IDord-c08d63c611c640118babbb95d0856f91
Source noteuspto-grants-2011_10