Dimethylformamide → t-Butyl 4-(3-benzyl-4-chloro-3H-imidazo(4,5-c]pyridin-2-yl)piperazine-1-carboxylate

HRID 501444Notes

Reaction equation

[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.CN(C)C=O.[CH2:19]([N:26]1[C:30]2[C:31]([Cl:35])=[N:32][CH:33]=[CH:34][C:29]=2[NH:28][CH:27]1Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(OCC)(=O)C>[CH2:19]([N:26]1[C:30]2[C:31]([Cl:35])=[N:32][CH:33]=[CH:34][C:29]=2[N:28]=[C:27]1[N:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 150 °C

Procedure

0.094 g of t-butyl piperazine-1-carboxylate was added to a 1 ml N,N-dimethylformamide solution of 0.127 g of 3-benzyl-2,4-dichloro-1,3-dihydroimidazo[4,5-c]pyridine, and the mixture was heated at 150° C. for two hours. 25 ml of ethyl acetate was added to the mixture, and the organic layer was washed three times with 10 ml of water and then with 10 ml of an aqueous solution saturated with sodium chloride. The organic liquid was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography. Thus, 0.029 g of the title compound was obtained from the fraction eluted with ethyl acetate-hexane (3:2).

Workup

washthe organic layer was washed three times with 10 ml of water
dry with materialThe organic liquid was dried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-18f80efefcc84a9fb204b98854d12c0f
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07772226B2

Reaction notes

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