Benzenepropanoic acid → HCID 178520436, compound

HRID 1823787Notes

Reaction equation

HRID 1823787 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C.[NH2:21][C:22]1[NH:23][C:24]2[CH:30]=[C:29]([O:31][S:32]([C:35]3[CH:40]=[CH:39][C:38]([NH:41][CH:42]4[CH2:46][CH2:45][CH2:44][CH2:43]4)=[CH:37][CH:36]=3)(=[O:34])=[O:33])[CH:28]=[CH:27][C:25]=2[N:26]=1>CN(C)C=O>[C:1]1([CH2:7][CH2:8][C:9]([NH:21][C:22]2[NH:26][C:25]3[CH:27]=[CH:28][C:29]([O:31][S:32]([C:35]4[CH:36]=[CH:37][C:38]([NH:41][CH:42]5[CH2:46][CH2:45][CH2:44][CH2:43]5)=[CH:39][CH:40]=4)(=[O:33])=[O:34])=[CH:30][C:24]=3[N:23]=2)=[O:11])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 107Benzenepropanoic acidHCID 81531DiisopropylethylamineHCID 12018867HCID 12018867, compound

Product 1

HCID 178520436HCID 178520436, compoundYield 40.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-phenyl propionic acid (9.7 mg) in dry dimethylformamide (0.6 ml) was treated with N-{(dimethylamino)(1H-1,2,3-triazolo[4,5-b]pyridin-1-yl)methylene}-N-methylmethanaminium hexafluorophosphate N-oxide (21 mg) and diisopropylethylamine (12 μl). After stirring at ambient temperature for 30 minutes, 4-cyclopentylamino-benzenesulfonic acid 2-amino-3H-benzoimidazol-5-yl ester (20 mg) was added and the mixture stirred at room temperature for a further 3 hours. The solvent was removed under vacuo and the residue was purified by triggered LC/MS to give 4-cyclopentylamino-benzenesulfonic acid 2-(3-phenyl-propionylamino)-1H-benzoimidazol-5-yl ester as an off-white solid (11 mg). Mass spectrum: 505 [M+H]+; retention time=4.59 minutes.

Workup

  1. stirringthe mixture stirred at room temperature for a further 3 hours
  2. customThe solvent was removed under vacuo
  3. customthe residue was purified by triggered LC/MS

Sources & evidence

ORD record
ord-d72abd948d264ef8b8818648ac546aa0
Source dataset
uspto-grants-2006_05
Patent number
US07041668B2

Reaction notes

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