Water → t-Butyl 4-[1-(2-butynyl)-7-oxo-6,7-dihydro-1H-imidazo[4,5-d]pyridazin-2-yl]piperazine-1-carboxylate

HRID 1351078Notes

Reaction equation

Br[C:2]1[N:3]([CH2:12][C:13]#[C:14][CH3:15])[C:4]2[C:9](=[O:10])[NH:8][N:7]=[CH:6][C:5]=2[N:11]=1.C(=O)([O-])[O-].[K+].[K+].[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23].O>CN(C)C=O>[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][N:32]([C:2]2[N:3]([CH2:12][C:13]#[C:14][CH3:15])[C:4]3[C:9](=[O:10])[NH:8][N:7]=[CH:6][C:5]=3[N:11]=2)[CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:23])[CH3:24]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2.11 g of 2-bromo-3-(2-butyn-1-yl)-3,5-dihydro-imidazo[4,5-d]pyridazin-4-one, 1.64 g potassium carbonate and 1.91 g 1-tert.-butyloxycarbonyl-piperazine in 20 ml N,N-dimethylformamide is stirred for six hours at 80° C. After cooling to ambient temperature the reaction mixture is combined with water and the precipitate formed is suction filtered. The crude product is purified by chromatography over a silica gel column with methylene chloride/methanol (95:5 to 90:10).

Workup

temperatureAfter cooling to ambient temperature the reaction mixture
customthe precipitate formed
filtrationfiltered
customThe crude product is purified by chromatography over a silica gel column with methylene chloride/methanol (95:5 to 90:10)

Sources & evidence

ORD record: ord-f5ee32ff804e47448d864314888c0ce2
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07217711B2

Reaction notes

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