Potassium Carbonate → HCID 57472499, compound

HRID 501362Notes

Reaction equation

CN1CCCC1=O.[CH2:8]([N:12]1[C:20]2[C:19](=[O:21])[N:18]([CH3:22])[N:17]=[CH:16][C:15]=2[N:14]=[C:13]1Cl)[C:9]#[C:10][CH3:11].C(=O)([O-])[O-].[K+].[K+].[N:30]1([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1>O>[CH2:8]([N:12]1[C:20]2[C:19](=[O:21])[N:18]([CH3:22])[N:17]=[CH:16][C:15]=2[N:14]=[C:13]1[N:33]1[CH2:32][CH2:31][N:30]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:35][CH2:34]1)[C:9]#[C:10][CH3:11]

Participants

Conditions

Temperature: 130 °C

Procedure

5 ml of 1-methyl-2-pyrrolidone was added to a mixture consisting of 1.183 g of 3-(2-butynyl)-2-chloro-5-methyl-3,5-dihydroimidazo[4,5-d]pyridazin-4-one, 0.829 g of potassium carbonate, and 1.395 g of t-butyl piperazine-1-carboxylate under a nitrogen atmosphere. The resulting mixture was heated at 130° C. for 6 hours. The reaction mixture was cooled, and 50 ml of water was added thereto. Then, the mixture was extracted with 100 ml of ethyl acetate. The organic layer was washed twice with 50 ml of water and then with 50 ml of an aqueous solution saturated with sodium chloride. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography. Thus, 1.916 g of the title compound was obtained from the fraction eluted with hexane-ethyl acetate (1:4).

Workup

temperatureThe reaction mixture was cooled
extractionThen, the mixture was extracted with 100 ml of ethyl acetate
washThe organic layer was washed twice with 50 ml of water
dry with materialThe organic layer was dried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-039d43541c5d4769b0f13250e1acb338
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07772226B2

Reaction notes

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