Methanesulfonic Acid → N-(cyanomethyl)-1-[4'-(1-piperazinyl)[1,1'-biphenyl]-3-yl]-2-piperidinecarboxamide

HRID 1744162Notes

Reaction equation

HRID 1744162 reaction equation
[C:1]([CH2:3][NH:4][C:5]([CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][N:8]1[C:13]1[CH:14]=[C:15]([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:16]=[CH:17][CH:18]=1)=[O:6])#[N:2].CS(O)(=O)=O>O1CCOCC1>[C:1]([CH2:3][NH:4][C:5]([CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][N:8]1[C:13]1[CH:14]=[C:15]([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:16]=[CH:17][CH:18]=1)=[O:6])#[N:2]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 22236171Tert-butyl 4-[3'-(2-{[(cyanomethyl)amino]carbonyl}-1-piperidinyl)[1,1'-biphenyl]-4-yl]-1-piperazinecarboxylate

Product 1

HCID 22235838N-(cyanomethyl)-1-[4'-(1-piperazinyl)[1,1'-biphenyl]-3-yl]-2-piperidinecarboxamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 4-[3′-(2-{[(cyanomethyl)amino]carbonyl}-1-piperidinyl)[1,1′-biphenyl]-4-yl]-1-piperazinecarboxylate (249 mg, 0.51 mmol) in dioxane (5 mL) was added methanesulfonic acid (0.1 mL, 1.5 mmol). The mixture was stirred overnight, then partitioned between EtOAc and 1 M NaOH. The organic phase was washed with brine and dried over MgSO4. Purification by flash chromatography (5% MeOH/dichloromethane with 0.5% NH4OH) gave N-(cyanomethyl)-1-[4′-(1-piperazinyl)[1,1′-biphenyl]-3-yl]-2-piperidinecarboxamide.

Workup

  1. custompartitioned between EtOAc and 1 M NaOH
  2. washThe organic phase was washed with brine
  3. dry with materialdried over MgSO4
  4. customPurification by flash chromatography (5% MeOH/dichloromethane with 0.5% NH4OH)

Sources & evidence

ORD record
ord-052b5fd5f05e40d18c3235c3483d7559
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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