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

HRID 2390840
Notes
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Reaction equation

HRID 2390840 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 67070141N-[3-tert-butyl-2-methoxy-5-(2-methoxypyridin-3-yl)phenyl]-4-methanesulfonylamino-N-methylbenzamide

Product 1

HCID 67069871N-[3-tert-butyl-2-methoxy-5-(2-oxo-1,2-dihydropyridin-3-yl)phenyl]-4-methanesulfonylamino-N-methylbenzamideYield 94%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent
HCID 8857
Ethyl Acetate
Solvent

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

  1. temperatureThe reaction mixture was cooled to RT
  2. washwashed sequentially with water and saturated aqueous NaHCO3
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by SiO2 chromatography
  7. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes