Water → HCID 57642836, compound

HRID 2112923Notes

Reaction equation

[CH2:1]([N:5]1[C:9]2[C:10](Cl)=[N:11][CH:12]=[CH:13][C:8]=2[N:7]([CH3:15])[C:6]1=[O:16])[C:2]#[C:3][CH3:4].[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18].C(OCC)(=O)C.O>CN1CCCC1=O>[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][N:27]([C:10]2[C:9]3[N:5]([CH2:1][C:2]#[C:3][CH3:4])[C:6](=[O:16])[N:7]([CH3:15])[C:8]=3[CH:13]=[CH:12][N:11]=2)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

Participants

Conditions

Temperature: 180 °C

Procedure

A solution of 3-(2-butynyl)-4-chloro-1-methyl-1,3-dihydroimidazo[4.5-c]pyridin-2-one (compound 82d) (0.865 g) and piperazine-1-carboxylic acid t-butyl ester (4.57 g) in 1-methyl-2-pyrrolidone (2 mL) was heated at 180° C. for two hours under a nitrogen atmosphere. Piperazine-1-carboxylic acid t-butyl ester (5.00 g) was then added again, and this was heated at 180° C. for five hours. Ethyl acetate (400 mL) and water (200 mL) were added, and the organic layer was washed twice with 200 mL of water and then once with 200 mL of saturated aqueous sodium chloride solution, and then was dried over anhydrous magnesium sulfate. The organic layer was filtered and concentrated under reduced pressure, and the residue was purified by silica gel chromatography. The ethyl acetate:hexane 3:2 fraction gave the title compound (0.447 g).

Workup

washthe organic layer was washed twice with 200 mL of water
dry with materialonce with 200 mL of saturated aqueous sodium chloride solution, and then was dried over anhydrous magnesium sulfate
filtrationThe organic layer was filtered
concentrationconcentrated under reduced pressure
customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-48ad627b858b4650b3df4c6850360fad
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07524847B2

Reaction notes

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