Cesium carbonate → HCID 58834347, compound

HRID 1710643Notes

Reaction equation

HRID 1710643 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[NH:25][C:26](=[O:29])[CH2:27][O:28][C:23]=2[CH:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[Cl:20][C:21]1[CH:31]=[CH:30][C:24]2[N:25]([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:26](=[O:29])[CH2:27][O:28][C:23]=2[CH:22]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 118300867-Chloro-2H-1,4-benzoxazinHCID 210711262-Chloro-1-(4-(4-chloro-3-methoxyphenyl)piperazin-1-yl)ethanone

Product 1

HCID 58834347HCID 58834347, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-chloro-1-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-ethanone (1) (331 mg, 1.1 mmol, 1 equiv) in 5 ml of DMF, 4H-Benzo[1,4]oxazin-3-one (28) (200 mg, 1.1 mmol, 1.0 equiv) and cesium carbonate (710 mg, 2.2 mmol, 2 equiv) was stirred at RT overnight. The reaction solution was diluted with EtOAc, and the organic solution was washed with water. Purification of the crude reaction mixture using flash chromatography provided 7-chloro-4-{2-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-4H-benzo[1,4]oxazin-3-one (29): LCMS Retention time, 2.58 min.; LCMS observed (M+H)+: 450.

Workup

  1. washthe organic solution was washed with water
  2. customPurification of the crude
  3. customreaction mixture

Sources & evidence

ORD record
ord-f564eafd8bac4e5a8b59803d6ef64c51
Source dataset
uspto-grants-2010_09
Patent number
US07790726B2

Reaction notes

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