Hydrogen Bromide → N-[3-tert-butyl-2-methoxy-5-(2-oxo-1,2-dihydropyridin-3-yl)phenyl]-4-methanesulfonylamino-N-methylbenzamide

HRID 2390840Notes

Reaction equation

[C:1]([C:5]1[C:6]([O:34][CH3:35])=[C:7]([N:19]([CH3:33])[C:20](=[O:32])[C:21]2[CH:26]=[CH:25][C:24]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])=[CH:23][CH:22]=2)[CH:8]=[C:9]([C:11]2[C:12]([O:17]C)=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].Br>CC(O)=O.CCOC(C)=O>[C:1]([C:5]1[C:6]([O:34][CH3:35])=[C:7]([N:19]([CH3:33])[C:20](=[O:32])[C:21]2[CH:22]=[CH:23][C:24]([NH:27][S:28]([CH3:31])(=[O:29])=[O:30])=[CH:25][CH:26]=2)[CH:8]=[C:9]([C:11]2[C:12](=[O:17])[NH:13][CH:14]=[CH:15][CH:16]=2)[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 142 (0.17 g, 0.33 mmol) in HOAc (3 mL) was added concentrated aqueous HBr (48%, 0.11 mL), and the solution was heated in a sealed tube at 60° C. for 15 h. The reaction mixture was cooled to RT, diluted with EtOAc, and washed sequentially with water and saturated aqueous NaHCO3. The organic layer was dried (Na2SO4), filtered and concentrated. The crude residue was purified by SiO2 chromatography eluting with DCM/MeOH/NH4OH to afford 0.15 g (93%) of N-[3-tert-butyl-2-methoxy-5-(2-oxo-1,2-dihydropyridin-3-yl)phenyl]-4-methanesulfonylamino-N-methylbenzamide (I-104) as a white powder.

Workup

temperatureThe reaction mixture was cooled to RT
washwashed sequentially with water and saturated aqueous NaHCO3
dry with materialThe organic layer was dried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customThe crude residue was purified by SiO2 chromatography
washeluting with DCM/MeOH/NH4OH

Sources & evidence

ORD record: ord-5143f2b5d6a14833ad42d72953d7ad0b
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273773B2

Reaction notes

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