(S)-N-((3-(3-fluoro-4-(piperazin-1-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide → 9-(4-{4-[(5S)-5-(Acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl}-piperazin-1-yl)-8-fluoro-3-methyl-6-oxo-2,3-dihydro-6H-1-oxa-3,3a-diaza-phenalene-5-carboxylic Acid Ethyl Ester

HRID 1163334Notes

Reaction equation

HRID 1163334 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:17](=[O:18])[C:16]2[C:19]3[N:8]([N:9]([CH3:22])[CH2:10][O:11][C:12]=3[C:13](F)=[C:14]([F:20])[CH:15]=2)[CH:7]=1)=[O:5])[CH3:2].[F:23][C:24]1[CH:25]=[C:26]([N:36]2[CH2:40][C@H:39]([CH2:41][NH:42][C:43](=[O:45])[CH3:44])[O:38][C:37]2=[O:46])[CH:27]=[CH:28][C:29]=1[N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1>N1C=CC=CC=1.CS(C)=O>[CH2:1]([O:3][C:4]([C:6]1[C:17](=[O:18])[C:16]2[C:19]3[N:8]([N:9]([CH3:22])[CH2:10][O:11][C:12]=3[C:13]([N:33]3[CH2:34][CH2:35][N:30]([C:29]4[CH:28]=[CH:27][C:26]([N:36]5[CH2:40][C@H:39]([CH2:41][NH:42][C:43](=[O:45])[CH3:44])[O:38][C:37]5=[O:46])=[CH:25][C:24]=4[F:23])[CH2:31][CH2:32]3)=[C:14]([F:20])[CH:15]=2)[CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 10520848(S)-N-((3-(3-fluoro-4-(piperazin-1-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamideHCID 157222128,9-difluoro-3-methyl-6-oxo-2,3-dihydro-6H-1-oxa-3,3a-diaza-phenalene-5-carboxylic acid ethyl ester

Product 1

HCID 672742189-(4-{4-[(5S)-5-(Acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl}-piperazin-1-yl)-8-fluoro-3-methyl-6-oxo-2,3-dihydro-6H-1-oxa-3,3a-diaza-phenalene-5-carboxylic Acid Ethyl Ester

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 1049PyridineSolvent

Procedure

A solution of 100 mg 8,9-difluoro-3-methyl-6-oxo-2,3-dihydro-6H-1-oxa-3,3a-diaza-phenalene-5-carboxylic acid ethyl ester (0.32 mmol) and 216 mg of N-[{(5S)-3[3-fluoro-4-(1-piperazinyl)phenyl]-2-oxo-5-oxazolidinyl}-methyl]-acetamide (0.64 mmol) were dissolved in a mixture of 1 ml pyridine and 1 ml DMSO. The reaction was monitored by TLC. The DMSO was evaporated, the residue digested in water and the solid collected. The solid was purified by chromatography, using a 9/1 dichloromethane/methanol mixture as eluent.

Workup

  1. customThe DMSO was evaporated
  2. customthe residue digested in water and the solid collected
  3. customThe solid was purified by chromatography

Sources & evidence

ORD record
ord-5d538a8bb75345eb86d22d801b3b5cdd
Source dataset
uspto-grants-2010_10
Patent number
US07820823B2

Reaction notes

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