Hydantoin-5-acetic acid → 2-(2,5-dioxo-4-imidazolidinyl)-N-{4-[(2-isopropyl-1H-benzimidazol-1-yl)methyl]phenyl)acetamide

HRID 1071374Notes

Reaction equation

HRID 1071374 reaction equation
[NH:1]1[CH:7]([CH2:8][C:9]([OH:11])=O)[C:5](=[O:6])[NH:4][C:2]1=[O:3].[CH:12]([C:15]1[N:19]([CH2:20][C:21]2[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=2)[C:18]2[CH:28]=[CH:29][CH:30]=[CH:31][C:17]=2[N:16]=1)([CH3:14])[CH3:13]>CS(C)=O>[O:3]=[C:2]1[NH:1][CH:7]([CH2:8][C:9]([NH:25][C:24]2[CH:23]=[CH:22][C:21]([CH2:20][N:19]3[C:18]4[CH:28]=[CH:29][CH:30]=[CH:31][C:17]=4[N:16]=[C:15]3[CH:12]([CH3:14])[CH3:13])=[CH:27][CH:26]=2)=[O:11])[C:5](=[O:6])[NH:4]1

Participants

4

Reactant 2

HCID 95492Hydantoin-5-acetic acidHCID 223927884-[(2-isopropyl-1H-benzimidazol-1-yl)methyl]aniline

Product 1

HCID 101794262-(2,5-dioxo-4-imidazolidinyl)-N-{4-[(2-isopropyl-1H-benzimidazol-1-yl)methyl]phenyl)acetamideYield 90.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Commercially available (+/−)hydantoin-5-acetic acid (11 mg, 0.07 mmol) and 4-[(2-isopropyl-1H-benzimidazol-1-yl)methyl]aniline (30 mg, 0.06 mmol) were warmed in 1 mL dry DMSO until dissolved and coupled using GENERAL COUPLING METHOD A. Purified on silica gel using 5% MeOH in EtOAc to give 22 mg (89%) of a white solid. MS found:(M+H)+=406.

Workup

  1. dissolutionuntil dissolved
  2. customPurified on silica gel using 5% MeOH in EtOAc

Sources & evidence

ORD record
ord-06f7dd006fc54dac81a281c1998e099c
Source dataset
uspto-grants-2005_06
Patent number
US06906053B2

Reaction notes

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