Acetyl chloride → N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-dimethylaminocarbonyl-5-acetylaminobenzenesulfonamide

HRID 2301689Notes

Reaction equation

HRID 2301689 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][O:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[N:10]=[C:9]([NH:15][C:16]([NH:18][S:19]([C:22]2[CH:27]=[C:26]([NH2:28])[CH:25]=[CH:24][C:23]=2[C:29]([N:31]([CH3:33])[CH3:32])=[O:30])(=[O:21])=[O:20])=[O:17])[N:8]=1>CC(N(C)C)=O>[CH3:5][O:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[N:10]=[C:9]([NH:15][C:16]([NH:18][S:19]([C:22]2[CH:27]=[C:26]([NH:28][C:1](=[O:3])[CH3:2])[CH:25]=[CH:24][C:23]=2[C:29]([N:31]([CH3:33])[CH3:32])=[O:30])(=[O:21])=[O:20])=[O:17])[N:8]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 108627955-amino-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-dimethylaminocarbonylbenzenesulfonamide

Product 1

HCID 15240556N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-dimethylaminocarbonyl-5-acetylaminobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

0.13 ml of acetyl chloride is slowly added dropwise to a mixture of 0.64 g of N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-5-amino-2-dimethylaminocarbonylbenzenesulfonamide and 10 ml of dimethylacetamide. After the end of reaction, the reaction mixture is concentrated under reduced pressure and the residue is washed with water and ethyl acetate, to give 0.45 g of the desired product in high purity (>92%, HPLC).

Workup

  1. customAfter the end of reaction
  2. concentrationthe reaction mixture is concentrated under reduced pressure
  3. washthe residue is washed with water and ethyl acetate

Sources & evidence

ORD record
ord-6eb23567464747e2bfb85ddef54ac80b
Source dataset
uspto-grants-2002_12
Patent number
US06500952B1

Reaction notes

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