Piperidine → 2-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-N-[5-[(E)-N'-hydroxycarbamimidoyl]pyrazin-2-yl]propanamide

HRID 719914Notes

Reaction equation

HRID 719914 reaction equation
Cl[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]([C:22]#[N:23])=[CH:18][N:17]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].[ClH:30].[NH2:31][OH:32].N1CCCCC1>CS(C)=O.O>[Cl:30][C:6]1[CH:5]=[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]([C:22](=[NH:23])[NH:31][OH:32])=[CH:18][N:17]=2)=[O:14])[CH:3]=[CH:2][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9]

Participants

6

Reactant 3

HCID 8082PiperidineHCID 443297Hydroxyamine hydrochlorideHCID 21897310HCID 21897310, compound

Product 1

HCID 1785047302-(3-chloro-4-methylsulfonylphenyl)-3-cyclopentyl-N-[5-[(E)-N'-hydroxycarbamimidoyl]pyrazin-2-yl]propanamideYield 63.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-(3-chloro-4-methanesulfonyl-phenyl)-N-(5-cyano-pyrazin-2-yl)-3-cyclopentyl-propionamide (400.0 mg, 0.924 mmol) in dimethyl sulfoxide (6 mL) at 25° C. was treated with hydroxylamine hydrochloride (330.0 mg, 4.749 mmol). The reaction mixture was then treated with piperidine (500 μL, 5.056 mmol) and then was stirred at 25° C. for 1 h. The reaction mixture was then diluted with water and then extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40L, Silica, 1/1 to 2/1 ethyl acetate/hexanes) afforded the 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(N-hydroxy-carbamimidoyl)-pyrazin-2-yl]-propionamide (274.5 mg, 63.8%) as a white solid: (ES)+-HRMS m/e calcd for C20H24ClN5O4S (M+H)+ 466.1311, found 466.1315.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bf5e46f774b3427cb0720baee833b4f4
Source dataset
uspto-grants-2006_11
Patent number
US07132425B2

Reaction notes

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