Chlorosuccinimide → HCID 59732932, compound

HRID 131978Notes

Reaction equation

HRID 131978 reaction equation
[CH:1]1([C:6]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=2[NH:15][C:16](=[O:27])[NH:17][C:18]2[S:19][CH:20]=[C:21]([CH2:23][C:24]([OH:26])=[O:25])[N:22]=2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:28]N1C(=O)CCC1=O>C(#N)C>[Cl:28][C:20]1[S:19][C:18]([NH:17][C:16]([NH:15][C:9]2[CH:10]=[CH:11][C:12]([CH3:14])=[CH:13][C:8]=2[C:6]([CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:7])=[O:27])=[N:22][C:21]=1[CH2:23][C:24]([OH:26])=[O:25]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 59732980HCID 59732980, compound

Product 1

HCID 59732932HCID 59732932, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of {2-[3-(2-cyclopentanecarbonyl-4-methyl-phenyl)-ureido]-thiazol-4-yl}-acetic acid (0.50 g, 1.29 mmol) in 20 ml of acetonitrile was added N-chlorosuccinimide (0.19 g, 1.42 mmol). The reaction mixture was stirred under nitrogen, in a pressure bottle excluded from light, for 2 h at 80° C. The mixture was concentrated under reduced pressure, dissolved in DMSO and purified by preparative HPLC to afford the title compound (0.128 g, 24%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutiondissolved in DMSO
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-de2c1c43f22d409cae6cf373a64da3e7
Source dataset
uspto-grants-2008_06
Patent number
US07384967B2

Reaction notes

Loading…