Diisopropyl Ether → Ethyl 8-(cyclohexylmethoxy)-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate

HRID 64400

Reaction equation

[CH:1]1([CH2:7][O:8][C:9]2[C:10]([NH2:16])=[N:11][CH:12]=[C:13]([CH3:15])[CH:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH:18]([C:24](=O)[CH3:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20].C(N(CC)CC)C.C(OC(C)C)(C)C>C1(C)C=CC=CC=1.O>[CH:1]1([CH2:7][O:8][C:9]2[C:10]3[N:11]([C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:24]([CH3:25])[N:16]=3)[CH:12]=[C:13]([CH3:15])[CH:14]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 1.38 g of 3-(cyclohexylmethoxy)-5-methylpyridin-2-amine in 24 ml of toluene were added 1.21 ml of ethyl 2-chloro-3-oxobutanoate and 1.23 ml of triethylamine, followed by stirring at 110° C. for 3 days. After leaving to be cooled at room temperature, water and diisopropyl ether were added thereto to carry out a layer separation operation. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 1.52 g of ethyl 8-(cyclohexylmethoxy)-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate.

Workup

customAfter leaving
temperatureto be cooled at room temperature
customa layer separation operation
dry with materialThe organic layer was dried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-d2d55b23c17241fd92a6743415c415e4
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447090B2

Linked notes

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