Iodoethane → 1-Ethyl-3-(3-{2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]ethyl}phenyl)-2-imidazolidinone hydrochloride

HRID 2373658Notes

Reaction equation

HRID 2373658 reaction equation
[ClH:1].Cl.[CH3:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[N:14]2[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][C:22]3[CH:23]=[C:24]([N:28]4[CH2:32][CH2:31][NH:30][C:29]4=[O:33])[CH:25]=[CH:26][CH:27]=3)[CH2:16][CH2:15]2)[N:5]=1.[H-].[Na+].I[CH2:37][CH3:38]>CN(C=O)C.CO>[ClH:1].[CH2:37]([N:30]1[CH2:31][CH2:32][N:28]([C:24]2[CH:25]=[CH:26][CH:27]=[C:22]([CH2:21][CH2:20][N:17]3[CH2:18][CH2:19][N:14]([C:10]4[CH:9]=[CH:8][CH:7]=[C:6]5[C:11]=4[CH:12]=[CH:13][C:4]([CH3:3])=[N:5]5)[CH2:15][CH2:16]3)[CH:23]=2)[C:29]1=[O:33])[CH3:38]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 49836021GSK163090 (dihydrochloride)

Product 1

HCID 574443681-Ethyl-3-(3-{2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]ethyl}phenyl)-2-imidazolidinone hydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1-(3-{2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]ethyl}phenyl)-2-imidazolidinone (Example 85, 50 mg) in DMF (1 mL) was added sodium hydride (60%, 10 mg). The mixture was stirred for 15 minutes, then iodoethane (11 □L) was added. The mixture was stirred for 90 minutes then diluted with methanol (5 mL) and purified by ion exchange chromatography [SCX-2; MeOH-(1M NH3/MeOH): (100:0)→(0:100)]. The basic washings were concentrated in vacuo and purified by column chromatography [SiO2; cyclohexane-EtOAc-MeOH: (1:1:0)→(0:10:1)] and converted to the hydrochloride salt according to the description given in the general procedure (D6) to give the title compound (49 mg).

Workup

  1. stirringThe mixture was stirred for 90 minutes
  2. custompurified by ion exchange chromatography [SCX-2; MeOH-(1M NH3/MeOH): (100:0)→(0:100)]
  3. concentrationThe basic washings were concentrated in vacuo
  4. custompurified by column chromatography [SiO2; cyclohexane-EtOAc-MeOH: (1:1:0)→(0:10:1)]

Sources & evidence

ORD record
ord-0ed37405670f451cb59652133c8c8ba2
Source dataset
uspto-grants-2008_12
Patent number
US07459456B2

Reaction notes

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