Methyl iodide → 1-Methyl-3-(3-{2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]ethyl}phenyl)-2-imidazolidinone

HRID 2373633Notes

Reaction equation

HRID 2373633 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][C:20]3[CH:21]=[C:22]([N:26]4[CH2:30][CH2:29][NH:28][C:27]4=[O:31])[CH:23]=[CH:24][CH:25]=3)[CH2:14][CH2:13]2)[N:3]=1.[CH3:32]I.[H-].[Na+]>C1COCC1>[CH3:32][N:28]1[CH2:29][CH2:30][N:26]([C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([CH2:19][CH2:18][N:15]3[CH2:16][CH2:17][N:12]([C:8]4[CH:7]=[CH:6][CH:5]=[C:4]5[C:9]=4[CH:10]=[CH:11][C:2]([CH3:1])=[N:3]5)[CH2:13][CH2:14]3)[CH:21]=2)[C:27]1=[O:31]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11292933Gsk163090

Product 1

HCID 112818241-Methyl-3-(3-{2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]ethyl}phenyl)-2-imidazolidinoneYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-(3-{2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]ethyl}phenyl)-2-imidazolidinone (E85) in THF was added methyl iodide (1 eq.), followed by sodium hydride (1.2 eq), and the reaction was stirred for 60 minutes. The mixture was loaded onto an ion-exchange cartridge (SCX-2) and eluted with methanol followed by ammonia in methanol (1M). The basic fractions were concentrated under vacuum and purified by column chromatography (SPE cartridge, Silica) using as eluent a gradient from DCM-methanol (99:1) to DCM-methanol (98:2) affording the final compound (45% yield).

Workup

  1. washeluted with methanol
  2. concentrationThe basic fractions were concentrated under vacuum
  3. custompurified by column chromatography (SPE cartridge, Silica)

Sources & evidence

ORD record
ord-26a0f4874e7c4ebfb8046afbf064e5e3
Source dataset
uspto-grants-2008_12
Patent number
US07459456B2

Reaction notes

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