Acetic Acid → 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(2,4-dioxo-thiazolidin-5-ylmethyl)-pyrazin-2-yl]-propionamide

HRID 719880

Reaction equation

HRID 719880 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:30][CH:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)[C:13]([NH:15][C:16]2[CH:21]=[N:20][C:19]([CH:22]=[C:23]3[S:27][C:26](=[O:28])[NH:25][C:24]3=[O:29])=[CH:18][N:17]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].C(OC(C1CC(C(OCC)=O)=C(C)NC=1C)=O)C.C(O)(=O)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:30][CH:31]2[CH2:32][CH2:33][CH2:34][CH2:35]2)[C:13]([NH:15][C:16]2[CH:21]=[N:20][C:19]([CH2:22][CH:23]3[S:27][C:26](=[O:28])[NH:25][C:24]3=[O:29])=[CH:18][N:17]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 70849Hantzsch esterHCID 865937822-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(2,4-dioxo-thiazolidin-5-ylidenemethyl)-pyrazin-2-yl]-propionamide

Product 1

HCID 104598462-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(2,4-dioxo-thiazolidin-5-ylmethyl)-pyrazin-2-yl]-propionamideYield 57.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(2,4-dioxo-thiazolidin-5-ylidenemethyl)-pyrazin-2-yl]-propionamide (150 mg, 0.28 mmol), 2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester (92.5 mg, 0.37 mmol), and silica gel (450 mg) in anhydrous toluene (12 mL) was heated at 90° C. for 12 h. The reaction mixture was then allowed to cool to 25° C. and then was acidified to pH=2 with acetic acid. The silica gel was removed by filtration and washed with a small amount of methanol. The product was then extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 1/9 to 7/3 ethyl acetate/hexanes) afforded the 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(2,4-dioxo-thiazolidin-5-ylmethyl)-pyrazin-2-yl]-propionamide (86.5 mg, 57%) as a white solid: LC-MS m/e 537 (MH+).

Workup

  1. temperatureto cool to 25° C.
  2. customThe silica gel was removed by filtration
  3. washwashed with a small amount of methanol
  4. extractionThe product was then extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2b6b6570f6e44b35883e2efd3eb5e926
Source dataset
uspto-grants-2006_11
Patent number
US07132425B2

Linked notes

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