Cesium carbonate → HCID 16059628, compound

HRID 1710645Notes

Reaction equation

HRID 1710645 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].[C:20]1([CH:26]2[CH2:30][O:29][C:28](=[O:31])[NH:27]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([N:8]2[CH2:9][CH2:10][N:5]([C:3](=[O:4])[CH2:2][N:27]3[CH:26]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH2:30][O:29][C:28]3=[O:31])[CH2:6][CH2:7]2)=[CH:12][C:13]=1[O:18][CH3:19]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 3497284-Phenyloxazolidin-2-oneHCID 210711262-Chloro-1-(4-(4-chloro-3-methoxyphenyl)piperazin-1-yl)ethanone

Product 1

HCID 16059628HCID 16059628, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 42 was prepared according to the procedure described in Example 2 using 2-Chloro-1-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-ethanone (1) (0.1 mmol), 4-phenyl-oxazolidin-2-one and Cs2CO3 in DMF: HPLC retention time, 2.30 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, 430.2, found, 430.3.

Workup

  1. customHPLC retention time, 2.30 minutes (Agilent Zorbax SB-C18, 2.1×50 mm, 5μ, 35° C.)
  2. washa 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)

Sources & evidence

ORD record
ord-6e49b10480af4d29b9f183883f5e42b2
Source dataset
uspto-grants-2010_09
Patent number
US07790726B2

Reaction notes

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