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

HRID 2301691Notes

Reaction equation

HRID 2301691 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-71434d538caa437db01d5e2b2ae714b3
Source dataset
uspto-grants-2002_12
Patent number
US06500952B1

Reaction notes

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