Pyridine → 2-(4-tert-Butylbenzoylamino)-5-methylsulfonylamino-N-(4-methoxyphenyl)benzamide

HRID 395718Notes

Reaction equation

HRID 395718 reaction equation
[C:1]([C:5]1[CH:31]=[CH:30][C:8]([C:9]([NH:11][C:12]2[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][C:13]=2[C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[O:15])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>C(Cl)Cl>[C:1]([C:5]1[CH:31]=[CH:30][C:8]([C:9]([NH:11][C:12]2[CH:28]=[CH:27][C:26]([NH:29][S:39]([CH3:38])(=[O:41])=[O:40])=[CH:25][C:13]=2[C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[O:15])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 106456292-(4-tert-butylbenzoylamino)-5-amino-N-(4-methoxyphenyl)benzamide

Product 1

HCID 107438372-(4-tert-Butylbenzoylamino)-5-methylsulfonylamino-N-(4-methoxyphenyl)benzamideYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(4-tert-butylbenzoylamino)-5-amino-N-(4-methoxyphenyl)benzamide (150 mg, 0.36 mmol) in methylene chloride (5 mL) cooled to 0° C. was added pyridine (32 μl, 0.40 mmol) followed by-,methanesulfonyl chloride. (31 μl, 0.40 mmol). After 5 min, the reaction mixture was allowed to warm to room temperature and stirred for 30 min. The reaction mixture was diluted with methylene chloride and washed twice with water. The organic layer was dried (magnesium sulfate), filtered, and concentrated in vacuo. The residue was chromatographed (silica gel, 30% ethyl acetate/70% methylene chloride) to give 130 mg (73%) of the title compound.

Workup

  1. washwashed twice with water
  2. dry with materialThe organic layer was dried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed (silica gel, 30% ethyl acetate/70% methylene chloride)

Sources & evidence

ORD record
ord-e5a7c3d46ad54d3b90e0631d9b3b256f
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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