Potassium bis(trimethylsilyl)amide → 7-nitro-2-[3-(2-oxo-oxazolidin-3-yl)-propyl]-6-(4-o-tolyl-piperazin-1-yl)-2H-isoquinolin-1-one

HRID 1481871Notes

Reaction equation

HRID 1481871 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][NH:10][C:11]2=[O:14])=[CH:6][C:5]=1[N:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:27])[CH2:17][CH2:16]1)([O-:3])=[O:2].Br[CH2:29][CH2:30][CH2:31][N:32]1[CH2:36][CH2:35][O:34][C:33]1=[O:37].C[Si]([N-][Si](C)(C)C)(C)C.[K+]>CN(C=O)C>[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][N:10]([CH2:29][CH2:30][CH2:31][N:32]3[CH2:36][CH2:35][O:34][C:33]3=[O:37])[C:11]2=[O:14])=[CH:6][C:5]=1[N:15]1[CH2:16][CH2:17][N:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:27])[CH2:19][CH2:20]1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 431353983-(3-Bromopropyl)-1,3-oxazolidin-2-oneHCID 896906327-nitro-6-(4-o-tolyl-piperazin-1-yl)-2H-isoquinolin-1-one

Product 1

HCID 896904547-nitro-2-[3-(2-oxo-oxazolidin-3-yl)-propyl]-6-(4-o-tolyl-piperazin-1-yl)-2H-isoquinolin-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 7-nitro-6-(4-o-tolyl-piperazin-1-yl)-2H-isoquinolin-1-one (0.25 g, 0.68 mmol) in anhydrous DMF (10 mL), 3-(3-bromo-propyl)-oxazolidin-2-one (0.14 g, 0.68 mmol) was added followed by potassium bis(trimethylsilyl) amide (0.27 g, 1.37 mmol) at 0° C. under N2 atmosphere. The reaction mass allowed to stir at room temperature for 6 h. The progress of the reaction was monitored by LCMS analysis. Upon completion of the reaction, solvent was removed in vacuo. Residue obtained was quenched with water, and extracted in dichloromethane (3×75 mL). The combined extract was washed with water, brine solution and dried over anhydrous Na2SO4. The crude product obtained was purified by the flash column chromatography (230-400 size mesh) using 1.5-1.75% methanol in dichloromethane to afford the compound 7-nitro-2-[3-(2-oxo-oxazolidin-3-yl)-propyl]-6-(4-o-tolyl-piperazin-1-yl)-2H-isoquinolin-1-one. Yield (0.25 g, 75%; and off-color solid).

Workup

  1. customUpon completion of the reaction, solvent
  2. customwas removed in vacuo
  3. customResidue obtained
  4. customwas quenched with water
  5. extractionextracted in dichloromethane (3×75 mL)
  6. extractionThe combined extract
  7. washwas washed with water, brine solution
  8. dry with materialdried over anhydrous Na2SO4
  9. customThe crude product obtained
  10. customwas purified by the flash column chromatography (230-400 size mesh)

Sources & evidence

ORD record
ord-8414bc2c2f8e40df82348dc311c8e8db
Source dataset
uspto-grants-2016_08
Patent number
US09409897B2

Reaction notes

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