Potassium Carbonate → 5-Chloro-3-{2-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-1-methyl-1,3-dihydro-benzoimidazol-2-one

HRID 1710663Notes

Reaction equation

HRID 1710663 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([O:18][CH3:19])[CH:12]=2)[CH2:7][CH2:6]1)=[O:4].[Cl:20][C:21]1[CH:31]=[CH:30][C:24]2[N:25]([CH3:29])[C:26](=[O:28])[NH:27][C:23]=2[CH:22]=1.C([O-])([O-])=O.[K+].[K+]>CN1C(=O)CCC1>[Cl:20][C:21]1[CH:31]=[CH:30][C:24]2[N:25]([CH3:29])[C:26](=[O:28])[N:27]([CH2:2][C:3]([N:5]3[CH2:10][CH2:9][N:8]([C:11]4[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([O:18][CH3:19])[CH:12]=4)[CH2:7][CH2:6]3)=[O:4])[C:23]=2[CH:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 140429432H-Benzimidazol-2-one,5-chloro-1,3-dihydro-1-methyl-(9CI)HCID 210711262-Chloro-1-(4-(4-chloro-3-methoxyphenyl)piperazin-1-yl)ethanone

Product 1

HCID 160596925-Chloro-3-{2-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-1-methyl-1,3-dihydro-benzoimidazol-2-one

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

33 mg of 2-chloro-1-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-ethanone (1) (0.18 mmol, 1.00 equiv), 58 mg of 5-chloro-1-methyl-1,3-dihydro-benzoimidazol-2-one (0.19 mmol, 1.05 equiv), 100 mg of K2CO3 (0.72 mmol, 4.0 equiv), and 0.8 mL of NMP were combined in a 4 mL vial. The resultant mixture was heated at 60° C. in an oil bath overnight. The crude product was purified by reversed phase HPLC (acetonitrile —H2O with 0.1% TFA as the eluent) to yield 5-chloro-3-{2-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-1-methyl-1,3-dihydro-benzoimidazol-2-one (66): HPLC retention time=2.40 minutes (Agilent Zorbax SB-C18, 2.1×50 mm, 5μ, 35° C.) using 1 ml/min flow rate, a 2.5 minute gradient of 20% to 100% B with a 1.1 minute wash at 100% B (A=0.1% formic acid/5% acetonitrile/94.9% water, B=0.08% formic acid/5% water/94.9% acetonitrile); MS (ES) M+H expected=449.0, found=449.1.

Workup

  1. customThe crude product was purified by reversed phase HPLC (acetonitrile —H2O with 0.1% TFA as the eluent)

Sources & evidence

ORD record
ord-befe5f1e53e74ebdacffde73e042956e
Source dataset
uspto-grants-2010_09
Patent number
US07790726B2

Reaction notes

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