Methanesulfonic Acid → N1-(cyanomethyl)-N2-[4-(4-piperazin-1-ylphenyl)-1,2,5-oxadiazol-3-yl]leucinamide

HRID 1744128Notes

Reaction equation

HRID 1744128 reaction equation
[C:1]([CH2:3][NH:4][C:5](=[O:36])[C@H:6]([CH2:32][CH:33]([CH3:35])[CH3:34])[NH:7][C:8]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]3)=[CH:15][CH:14]=2)=[N:11][O:10][N:9]=1)#[N:2].CS(O)(=O)=O.C([O-])(O)=O.[Na+]>C1COCC1>[C:1]([CH2:3][NH:4][C:5](=[O:36])[C@H:6]([CH2:32][CH:33]([CH3:34])[CH3:35])[NH:7][C:8]1[C:12]([C:13]2[CH:14]=[CH:15][C:16]([N:19]3[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]3)=[CH:17][CH:18]=2)=[N:11][O:10][N:9]=1)#[N:2]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 516892Sodium BicarbonateHCID 86594573N1-(cyanomethyl)-N2-(4-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}-1,2,5-oxadiazol-3-yl)leucinamide

Product 1

HCID 86594574N1-(cyanomethyl)-N2-[4-(4-piperazin-1-ylphenyl)-1,2,5-oxadiazol-3-yl]leucinamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To N1-(cyanomethyl)-N2-(4-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}-1,2,5-oxadiazol-3-yl)leucinamide (170 mg, 0.33 mmol) in dry THF (1 mL) under dry nitrogen was gradually added a total of 6 equivalents of MeSO3H (120 μL, 2.0 mmol) over a period of 2 hours in portions of 2 equivalents at a time and the reaction mixture stirred overnight. Aqueous sat. NaHCO3 was added carefully and the product extracted with EtOAc (2×), dried over Na2SO4, concentrated in vacuo and purified by flash chromatography over silica gel (NH4OH/MeOH/CH2Cl2, 1/9/90) to afford N1-(cyanomethyl)-N2-[4-(4-piperazin-1-ylphenyl)-1,2,5-oxadiazol-3-yl]leucinamide.

Workup

  1. extractionthe product extracted with EtOAc (2×)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography over silica gel (NH4OH/MeOH/CH2Cl2, 1/9/90)

Sources & evidence

ORD record
ord-55ededccd4e6425d915e49d4e4f62525
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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