Water → 6-Iodoimidazo[1,2-B]pyridazin-2-amine

HRID 2391116Notes

Reaction equation

O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].O.[I:13][C:14]1[CH:15]=[CH:16][C:17]2[N:18]([CH:20]=[C:21]([NH:23]C(=O)OCC)[N:22]=2)[N:19]=1>CN1CCCC1=O>[I:13][C:14]1[CH:15]=[CH:16][C:17]2[N:18]([CH:20]=[C:21]([NH2:23])[N:22]=2)[N:19]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To barium hydroxide octahydrate (14.5 g, 46.1 mmol) was added water (240 mL), and the mixture was stirred at 80° C. for 15 min. A solution of ethyl (6-iodoimidazo[1,2-b]pyridazin-2-yl)carbamate (10.2 g, 30.7 mmol) in N-methylpyrrolidone (80 mL) was added to the mixture, and the mixture was stirred at 120° C. for 8 hr. After cooling the mixture to room temperature, water (480 mL) was added to the mixture, and the mixture was stirred for 1 hr. The mixture was extracted twice with ethyl acetate/tetrahydrofuran, washed with saturated brine, dried over anhydrous magnesium sulfate, and filtrated. The solvent was evaporated under reduced pressure, diisopropyl ether was added to the residue, and the precipitated crystals were collected by filtration to give the title compound (6.1 g, 76%) as a brown powder.

Workup

stirringthe mixture was stirred at 120° C. for 8 hr
temperatureAfter cooling the mixture to room temperature
stirringthe mixture was stirred for 1 hr
extractionThe mixture was extracted twice with ethyl acetate/tetrahydrofuran
washwashed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltrated
customThe solvent was evaporated under reduced pressure, diisopropyl ether
additionwas added to the residue
filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record: ord-a5c2901934e44137983ff6075af489d4
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273741B2

Reaction notes

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