Hydrogen Bromide → HCID 58452588, compound

HRID 70650Notes

Reaction equation

Br.[C:2]([C:6]1[CH:11]=[CH:10][C:9](/[C:12](/[C:20]2[CH:25]=[CH:24][C:23]([N:26]([CH3:28])[CH3:27])=[C:22]([O:29]C)[N:21]=2)=[CH:13]\[C@@H:14]2[NH:18][C:17](=[O:19])[CH2:16][CH2:15]2)=[CH:8][CH:7]=1)([CH3:5])([CH3:4])[CH3:3].O>O1CCOCC1>[C:2]([C:6]1[CH:7]=[CH:8][C:9](/[C:12](/[C:20]2[NH:21][C:22](=[O:29])[C:23]([N:26]([CH3:27])[CH3:28])=[CH:24][CH:25]=2)=[CH:13]\[C@H:14]2[CH2:15][CH2:16][C:17](=[O:19])[NH:18]2)=[CH:10][CH:11]=1)([CH3:5])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 65 °C

Procedure

48% hydrobromic acid (0.5 mL) was added to a solution of (5R)-5-{(E)-2-(4-tert-butylphenyl)-2-[5-(dimethylamino)-6-methoxypyridin-2-yl]ethenyl}pyrrolidin-2-one (41 mg) in 1,4-dioxane (1 mL), and the mixture was stirred at 65° C. for 30 minutes. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=10:0→4:1) and crystallized from chloroform-ethyl acetate to give the title compound as a light yellow powder (11 mg, 26% (two steps)).

Workup

extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over anhydrous magnesium sulfate
customafter which the solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (chloroform:methanol=10:0→4:1)
customcrystallized from chloroform-ethyl acetate

Sources & evidence

ORD record: ord-adfbd43f7e094221ba1b3c245e7f1512
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822503B2

Reaction notes

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