N-bromobutanimide → HCID 59732819, compound

HRID 131979Notes

Reaction equation

HRID 131979 reaction equation
C([O:3][C:4](=[O:29])[CH2:5][C:6]1[N:7]=[C:8]([NH:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=2[C:22]([CH:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)=[O:23])=[O:13])[S:9][CH:10]=1)C.[Br:30]N1C(=O)CCC1=O>C(O)(=O)C>[Br:30][C:10]1[S:9][C:8]([NH:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=2[C:22]([CH:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)=[O:23])=[O:13])=[N:7][C:6]=1[CH2:5][C:4]([OH:3])=[O:29]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 59732991HCID 59732991, compound

Product 1

HCID 59732819HCID 59732819, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a suspension of {2-[3-(2-cyclopentanecarbonyl-4-methyl-phenyl)-ureido]-thiazol-4-yl}-acetic acid ethyl ester (0.20 g, 0.52 mmol) in 10 ml of acetic acid was added N-bromosuccinimide (0.10 g, 0.57 mmol). The reaction mixture was stirred under nitrogen in a pressure bottle excluded from light overnight at 25° C. The mixture was concentrated under reduced pressure, dissolved in DMSO and purified by preparative HPLC to afford the title compound (0.137 g, 57%).

Workup

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

Sources & evidence

ORD record
ord-b29565ee7d7c4e73a2be88f56bce5851
Source dataset
uspto-grants-2008_06
Patent number
US07384967B2

Reaction notes

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