Pyridine → 5-Methanesulfonylamino-N-methyl-N-propyl-isophthalamic acid methyl ester

HRID 732513Notes

Reaction equation

HRID 732513 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:16]=[C:15]([NH2:17])[CH:14]=[C:6]([C:7]([N:9]([CH3:13])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=1.N1C=CC=CC=1.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>ClCCl>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:16]=[C:15]([NH:17][S:26]([CH3:25])(=[O:28])=[O:27])[CH:14]=[C:6]([C:7]([N:9]([CH3:13])[CH2:10][CH2:11][CH3:12])=[O:8])[CH:5]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 688147595-Amino-N-methyl-N-propyl-isophthalamic acid methyl ester

Product 1

HCID 688152395-Methanesulfonylamino-N-methyl-N-propyl-isophthalamic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dissolve 5-amino-N-methyl-N-propyl-isophthalamic acid methyl ester (1.64 g, 6.55 mmol) in dichloromethane (20 mL) and add pyridine (620 mg, 6.88 mmol) and methanesulfonyl chloride (788 mg, 6.88 mmol). Stir at room temperature for 72 h, dilute with dichloromethane, wash with 0.1 N citric acid and saturated aqueous sodium chloride. Dry (magnesium sulfate) and concentrate to give the title compound as an oil.

Workup

  1. washwash with 0.1 N citric acid and saturated aqueous sodium chloride
  2. dry with materialDry (magnesium sulfate)
  3. concentrationconcentrate

Sources & evidence

ORD record
ord-5ae49b24f6ea4ac59401f734c971467f
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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