Methanesulfonic Acid → HCID 10272809, compound

HRID 1744055Notes

Reaction equation

HRID 1744055 reaction equation
[C:1]([CH2:3][NH:4][C:5]([CH:7]([NH:12][C:13]1[N:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH2:26]3)=[CH:21][CH:20]=2)=[CH:15][N:14]=1)[CH2:8][CH:9]([CH3:11])[CH3:10])=[O:6])#[N:2].CS(O)(=O)=O.C([O-])(O)=O.[Na+]>C1COCC1>[C:1]([CH2:3][NH:4][C:5](=[O:6])[CH:7]([NH:12][C:13]1[N:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH2:26][CH2:27][NH:28][CH2:29][CH2:30]3)=[CH:21][CH:20]=2)=[CH:15][N:14]=1)[CH2:8][CH:9]([CH3:11])[CH3:10])#[N:2]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 516892Sodium BicarbonateHCID 22236145HCID 22236145, compound

Product 1

HCID 10272809HCID 10272809, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To tert-butyl 4-(4-{2-[(1-{[(cyanomethyl)amino]carbonyl}-3-methylbutyl)amino]-5-pyrimidinyl}phenyl)-1-piperazinecarboxylate (108 mg, 0.213 mmol) in dry THF (5 mL) under dry nitrogen was gradually added a total of 9 equivalents of MeSO3H (total of 125 μL, 1.92 mmol) over a period of 3 days in portions of 1–2 equivalents at a time. Aqueous sat. NaHCO3 was added carefully and the product extracted with EtOAc (3×), dried over Na2SO4, concentrated in vacuo, and purified by flash chromatography over silica gel (NH4OH/MeOH/CH2Cl2, 1/9/90) to afford N-(cyanomethyl)-4-methyl-2-({5-[4-(1-piperazinyl)phenyl]-2-pyrimidinyl}amino)pentanamide. MS (−ESI): 406.4 [M−1]−.

Workup

  1. extractionthe product extracted with EtOAc (3×)
  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-b0056e3dd6c548e297cf571f69c3a2ac
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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