Acetic Anhydride → 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(5-methyl-[1,2,4]oxadiazol-3-yl)-pyrazin-2-yl]-propionamide

HRID 719915Notes

Reaction equation

HRID 719915 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:26][CH:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)[C:13]([NH:15][C:16]2[CH:21]=[N:20][C:19]([C:22](=[NH:25])[NH:23][OH:24])=[CH:18][N:17]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].[C:32](OC(=O)C)(=O)[CH3:33]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:26][CH:27]2[CH2:28][CH2:29][CH2:30][CH2:31]2)[C:13]([NH:15][C:16]2[CH:21]=[N:20][C:19]([C:22]3[N:25]=[C:32]([CH3:33])[O:24][N:23]=3)=[CH:18][N:17]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:9])=[O:10]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 1785047302-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-N-[5-[(E)-N'-hydroxycarbamimidoyl]pyrazin-2-yl]propanamide

Product 1

HCID 218972962-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(5-methyl-[1,2,4]oxadiazol-3-yl)-pyrazin-2-yl]-propionamideYield 21.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(N-hydroxycarbamimidoyl)-pyrazin-2-yl]-propionamide (197.0 mg, 0.423 mmol) and acetic anhydride (970 μL, 10.281 mmol) was placed into a one-dram glass vial. The vial was tightly sealed, and the reaction was stirred at 120° C. for 3.5 h. The reaction was diluted with ethyl acetate (75 mL) and washed with a saturated aqueous sodium bicarbonate solution (50 mL) and a saturated aqueous sodium chloride solution (50 mL). The combined aqueous layers were back-extracted with ethyl acetate (50 mL). The resulting combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40L, Silica, 1/1 ethyl acetate/hexanes) afforded 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(5-methyl-[1,2,4]oxadiazol-3-yl)-pyrazin-2-yl]-propionamide (43.8 mg, 21%) as a white foam; mp 101.9–104.8° C. (foam to gel); (ES)+-HRMS m/e calcd for C22H24ClN5O4S (M+H)+ 490.1311, found 490.1315.

Workup

  1. customThe vial was tightly sealed
  2. washwashed with a saturated aqueous sodium bicarbonate solution (50 mL)
  3. extractionThe combined aqueous layers were back-extracted with ethyl acetate (50 mL)
  4. dry with materialwere dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e22025e11a28447192361dffae2b4e09
Source dataset
uspto-grants-2006_11
Patent number
US07132425B2

Reaction notes

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