Hydrogen Bromide → HCID 67398115, compound

HRID 70691Notes

Reaction equation

Br.[Cl:2][C:3]1[CH:8]=[CH:7][C:6](/[C:9](/[C:28]2[CH:33]=[CH:32][C:31]([C:34]3[CH:35]=[N:36][NH:37][CH:38]=3)=[C:30]([O:39]C)[N:29]=2)=[CH:10]\[C@@H:11]2[N:15]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=3[O:25][CH3:26])[C:14](=[O:27])[CH2:13][CH2:12]2)=[CH:5][CH:4]=1.O>O1CCOCC1>[Cl:2][C:3]1[CH:4]=[CH:5][C:6](/[C:9](/[C:28]2[NH:29][C:30](=[O:39])[C:31]([C:34]3[CH:38]=[N:37][NH:36][CH:35]=3)=[CH:32][CH:33]=2)=[CH:10]\[C@H:11]2[CH2:12][CH2:13][C:14](=[O:27])[N:15]2[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=2[O:25][CH3:26])=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 65 °C

Procedure

48% hydrobromic acid (1.25 mL) was added to a solution of (5R)-5-{(E)-2-(4-chlorophenyl)-2-[6-methoxy-5-(1H-pyrazol-4-yl)pyridin-2-yl]ethenyl}-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one (63 mg) in 1,4-dioxane (1.25 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 resulting residue was purified by silica gel column chromatography (chloroform:methanol=10:0→9:1) to give 6-{(E)-1-(4-chlorophenyl)-2-[(2R)-1-(2,4-dimethoxybenzyl)-5-oxopyrrolidin-2-yl]ethenyl}-3-(1H-pyrazol-4-yl)pyridin-2(1H)-one as a yellow amorphous (100 mg, 81%).

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 resulting residue was purified by silica gel column chromatography (chloroform:methanol=10:0→9:1)

Sources & evidence

ORD record: ord-6a51086b68b44228984e9ec4e1070222
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822503B2

Reaction notes

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