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Methanesulfonyl chloride → N-[3-tert-butyl-2-methoxy-5-(2-methoxypyridin-3-yl)phenyl]-4-methanesulfonylaminobenzamide

HRID 2390822
Notes
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Reaction equation

HRID 2390822 reaction equation
[NH2:1][C:2]1[CH:30]=[CH:29][C:5]([C:6]([NH:8][C:9]2[CH:14]=[C:13]([C:15]3[C:16]([O:21][CH3:22])=[N:17][CH:18]=[CH:19][CH:20]=3)[CH:12]=[C:11]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:10]=2[O:27][CH3:28])=[O:7])=[CH:4][CH:3]=1.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>N1C=CC=CC=1.CCOC(C)=O>[C:23]([C:11]1[C:10]([O:27][CH3:28])=[C:9]([NH:8][C:6](=[O:7])[C:5]2[CH:29]=[CH:30][C:2]([NH:1][S:32]([CH3:31])(=[O:34])=[O:33])=[CH:3][CH:4]=2)[CH:14]=[C:13]([C:15]2[C:16]([O:21][CH3:22])=[N:17][CH:18]=[CH:19][CH:20]=2)[CH:12]=1)([CH3:26])([CH3:24])[CH3:25]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 670700384-amino-N-[3-tert-butyl-2-methoxy-5-(2-methoxypyridin-3-yl)phenyl]benzamide

Product 1

HCID 67286646N-[3-tert-butyl-2-methoxy-5-(2-methoxypyridin-3-yl)phenyl]-4-methanesulfonylaminobenzamideYield 99.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent
HCID 8857
Ethyl Acetate
Solvent

Procedure

step 5—To a solution of 104 (0.10 g, 0.25 mmol) in pyridine (2 mL) at 0° C. was added methanesulfonyl chloride (0.034 g, 0.30 mmol). Stirring was continued at 0° C. for two h, then at RT for an additional two h. The reaction mixture was diluted with EtOAc, washed sequentially with aqueous CuSO4 and 2N HCl, dried (Na2SO4), filtered and concentrated. The crude residue was purified by SiO2 chromatography (EtOAc/hexane) to afford 0.12 g of N-[3-tert-butyl-2-methoxy-5-(2-methoxypyridin-3-yl)phenyl]-4-methanesulfonylaminobenzamide (106) as a colorless oil.

Workup

  1. customwas continued at 0° C. for two h
  2. washwashed sequentially with aqueous CuSO4 and 2N HCl
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by SiO2 chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-afe6849bfd304e51a8973ede2ac57564
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08273773B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes