Ethyl isocyanatoacetate → {3-[5-(4-Dimethylsulfamoyl-phenyl)-4-methyl-thiazol-2-yl]-ureido}-acetic acid ethyl ester

HRID 1092942Notes

Reaction equation

HRID 1092942 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([N:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[C:5]([CH3:7])[N:6]=1.[N:20]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:21]=[O:22]>CN(C)C=O>[CH2:27]([O:26][C:24](=[O:25])[CH2:23][NH:20][C:21]([NH:1][C:2]1[S:3][C:4]([C:8]2[CH:9]=[CH:10][C:11]([S:14](=[O:15])(=[O:16])[N:17]([CH3:18])[CH3:19])=[CH:12][CH:13]=2)=[C:5]([CH3:7])[N:6]=1)=[O:22])[CH3:28]

Participants

4

Reactant 2

HCID 76283Ethyl isocyanatoacetateHCID 858617264-(2-Amino-4-methyl-thiazol-5-yl)-N,N-dimethyl-benzenesulfonamide

Product 1

HCID 86598400{3-[5-(4-Dimethylsulfamoyl-phenyl)-4-methyl-thiazol-2-yl]-ureido}-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(2-Amino-4-methyl-thiazol-5-yl)-N,N-dimethyl-benzenesulfonamide (Example 24a) (0.083 g, 0.28 mmol) and ethyl isocyanatoacetate (0.05 ml, 0.34 mmol) are stirred in dimethylformamide at 100° C. for 3 hours. The mixture is then partitioned between 1M aqueous hydrochloric acid and ethyl acetate. The organic extract is washed with brine, dried over MgSO4 and the solvent removed in vacuo. Purification by preparative HPLC affords the title compound. MH+ (TOF, MS, ES+): 441.4

Workup

  1. customThe mixture is then partitioned between 1M aqueous hydrochloric acid and ethyl acetate
  2. extractionThe organic extract
  3. washis washed with brine
  4. dry with materialdried over MgSO4
  5. customthe solvent removed in vacuo
  6. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-fa81f0b85e084cdb82bc553a9b4f641e
Source dataset
uspto-grants-2012_03
Patent number
US08129541B2

Reaction notes

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