Water → HCID 24852561, compound

HRID 599562Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:18]3[CH2:19][CH2:20][CH2:21]/[C:22](=[CH:23]\[C:24]4[CH:29]=[CH:28][C:27]([N:30]5[CH:34]=[C:33]([CH3:35])[N:32]=[CH:31]5)=[C:26]([O:36][CH3:37])[CH:25]=4)/[C:17]3=[N:16][C:15]=2[C:38](OC)=[O:39])=[CH:10][CH:9]=1.C(OCC)(=O)C.O>C1COCC1>[F:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[N:18]3[CH2:19][CH2:20][CH2:21]/[C:22](=[CH:23]\[C:24]4[CH:29]=[CH:28][C:27]([N:30]5[CH:34]=[C:33]([CH3:35])[N:32]=[CH:31]5)=[C:26]([O:36][CH3:37])[CH:25]=4)/[C:17]3=[N:16][C:15]=2[CH2:38][OH:39])=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

LAH (7 mg) was added to a solution of methyl 3-(4-fluorophenyl)-8-{1-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-(E)-methylidene}-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carboxylate (86 mg) in THF (3 mL), and the reaction solution was stirred at 0° C. for one hour. Ethyl acetate and water were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: ethyl acetate→ethyl acetate:methanol=5:1) to obtain 25 mg of the title compound. The property values of the compound are as follows.

Workup

customthe organic layer was separated
dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate→ethyl acetate:methanol=5:1)

Sources & evidence

ORD record: ord-3a9f22a4ae144500aba7d72a4f2db252
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897632B2

Reaction notes

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