Benzoic Acid → 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(2,5-dioxo-imidazolidin-4-ylidenemethyl)-pyrazin-2-yl]-propionamide

HRID 719881Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:24][CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)[C:13]([NH:15][C:16]2[CH:21]=[N:20][C:19]([CH:22]=O)=[CH:18][N:17]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].[NH:30]1[CH2:36][C:34](=[O:35])[NH:33][C:31]1=[O:32].N1CCCCC1.C(O)(=O)C1C=CC=CC=1>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:24][CH:25]2[CH2:26][CH2:27][CH2:28][CH2:29]2)[C:13]([NH:15][C:16]2[CH:21]=[N:20][C:19]([CH:22]=[C:36]3[C:34](=[O:35])[NH:33][C:31](=[O:32])[NH:30]3)=[CH:18][N:17]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:9])=[O:10]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-(5-formyl-pyrazin-2-yl)-propionamide (prepared as in Example 18, 217 mg, 0.5 mmol), hydantoin (75 mg, 0.75 mmol), piperidine (10 μL, 0.10 mmol), and benzoic acid (6.1 mg, 0.05 mmol) in anhydrous ethanol (30 mL) was heated under reflux for 2 d. The reaction mixture was allowed to cool to 25° C. and then was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 10%–65% ethyl acetate/hexanes) afforded the 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(2,5-dioxo-imidazolidin-4-ylidenemethyl)-pyrazin-2-yl]-propionamide (84 mg, 33%) as a white solid: LC-MS m/e 518 (MH+).

Workup

temperatureunder reflux for 2 d
concentrationwas concentrated in vacuo

Sources & evidence

ORD record: ord-031dcd7d4b9f4c91bc25113b77c57376
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07132425B2

Reaction notes

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