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

HRID 2247323Notes

Reaction equation

HRID 2247323 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-3281ba6822614a76bb7e4f8bb21e482d
Source dataset
uspto-grants-2010_03
Patent number
US07687637B2

Reaction notes

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