Methanesulfonic Acid → HCID 178445938, compound

HRID 1744135Notes

Reaction equation

HRID 1744135 reaction equation
[C:1]([CH2:3][NH:4][C:5](=[O:43])[C@H:6]([CH2:39][CH:40]([CH3:42])[CH3:41])[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)=[CH:11][N:10](C(OC(C)(C)C)=O)[N:9]=1)#[N:2].CS(O)(=O)=O.C([O-])(O)=O.[Na+]>C1COCC1>[C:1]([CH2:3][NH:4][C:5](=[O:43])[C@H:6]([CH2:39][CH:40]([CH3:41])[CH3:42])[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)=[CH:11][NH:10][N:9]=1)#[N:2]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 516892Sodium BicarbonateHCID 86594575HCID 86594575, compound

Product 1

HCID 178445938HCID 178445938, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To N1-(cyanomethyl)-N2-(1-(tert-butoxycarbonyl)-4-{4-[4-(tert-butoxycarbonyl)piperazin-1-yl]phenyl}-1H-pyrazol-3-yl)leucinamide (163 mg, 0.274 mmol) in dry THF (0.5 mL) under dry nitrogen was gradually added a total of 5 equivalents of MeSO3H (100 μL, 1.37 mmol) over a period of 3 hours in portions of 1–2 equivalents at a time and the reaction mixture was 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)-1H-pyrazol-3-yl]leucinamide. MS (+ESI): 398.4 [M+1]+.

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-4df699cab3b74342a3f3ea96de5179d7
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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