Dimethylformamide → HCID 16059627, compound

HRID 1710646Notes

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(N2CCOC2=O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[C:32]([O-])([O-])=[O:33].[Cs+].[Cs+].C[N:39]([CH:41]=[O:42])[CH3:40]>>[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:39]3[CH2:40][CH:32]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)[O:33][C:41]3=[O:42])[CH2:6][CH2:7]2)=[CH:12][C:13]=1[O:18][CH3:19]

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 10796Cesium carbonate

HCID 1365473-Phenyl-2-oxazolidinone

HCID 210711262-Chloro-1-(4-(4-chloro-3-methoxyphenyl)piperazin-1-yl)ethanone

Product 1

HCID 16059627HCID 16059627, compound

Procedure

Compound 43 was prepared according to the procedure described Example 2 using 2-Chloro-1-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-ethanone (1) (0.1 mmol), 3-phenyl-oxazolidin-2-one and Cs2CO3 in DMF: HPLC retention time, 2.32 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, 430.2.

Workup

customHPLC retention time, 2.32 minutes (Agilent Zorbax SB-C18, 2.1×50 mm, 5μ, 35° C.)
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-e02fa368bb794f7ab0810bc929142494
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790726B2

Reaction notes

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