Methyl iodide → HCID 16059503, compound

HRID 1710636Notes

Reaction equation

HRID 1710636 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:26])[CH2:15][N:16]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[NH:18][C:17]3=[O:25])[CH2:10][CH2:9]2)=[CH:4][C:3]=1[O:27][CH3:28].IC.[C:31]([O-])([O-])=O.[Cs+].[Cs+]>CN1C(=O)CCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:9][CH2:10][N:11]([C:14](=[O:26])[CH2:15][N:16]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[N:18]([CH3:31])[C:17]3=[O:25])[CH2:12][CH2:13]2)=[CH:4][C:3]=1[O:27][CH3:28]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 58834348HCID 58834348, compound

Product 1

HCID 16059503HCID 16059503, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

In a 4 mL vial was added 1-{2-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-1,3-dihydro-benzoimidazol-2-one (19) (10 mg, 0.025 mmol, 1.0 equiv), 5 μL of iodomethane (0.081 mmol, 3.26 equiv), 25 mg Cs2CO3 (0.075 mmol, 3.00 equiv) and 150 μL of NMP. A stir bar was placed in the vial and the vial was then capped. The resultant mixture stirred at 60° C. overnight. The crude product was purified by reversed phase HPLC (acetonitrile —H2O with 0.1% TFA as the eluent) to yield 1-{2-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-3-methyl-1,3-dihydro-benzoimidazol-2-one (20): HPLC retention time, 2.14 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=0.1% formic acid/5% water/94.9% acetonitrile); MS (ES) M+H expected, 414.9, found, 415.5.

Workup

  1. customA stir bar was placed
  2. customin the vial and the vial was then capped
  3. customThe crude product was purified by reversed phase HPLC (acetonitrile —H2O with 0.1% TFA as the eluent)

Sources & evidence

ORD record
ord-5be4b29a6f69418390b9990966d3c6ac
Source dataset
uspto-grants-2010_09
Patent number
US07790726B2

Reaction notes

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