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

HRID 1006582Notes

Reaction equation

HRID 1006582 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[NH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:30]([N:32]([CH3:34])[CH3:33])=[O:31])=[C:11]([S:13]([NH:16][C:17]([NH:19][C:20]2[N:25]=[C:24]([O:26][CH3:27])[CH:23]=[C:22]([O:28][CH3:29])[N:21]=2)=[O:18])(=[O:15])=[O:14])[CH:12]=1>CC(N(C)C)=O>[CH3:27][O:26][C:24]1[CH:23]=[C:22]([O:28][CH3:29])[N:21]=[C:20]([NH:19][C:17]([NH:16][S:13]([C:11]2[CH:12]=[C:7]([NH:6][C:1](=[O:4])[CH2:2][CH3:3])[CH:8]=[CH:9][C:10]=2[C:30]([N:32]([CH3:34])[CH3:33])=[O:31])(=[O:15])=[O:14])=[O:18])[N:25]=1

Participants

4

Reactant 2

HCID 62324Propionyl chlorideHCID 108627955-amino-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-dimethylaminocarbonylbenzenesulfonamide

Product 1

HCID 15240552N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-dimethylaminocarbonyl-5-propionylaminobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

0.13 ml of propionyl chloride is added slowly dropwise to a solution of 0.64 g of 5-amino-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-dimethylaminocarbonylbenzenesulfonamide in 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-cd3985202cab46c1b257d4ea423563c9
Source dataset
uspto-grants-2004_09
Patent number
US06790955B2

Reaction notes

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