Methanesulfonyl chloride → HCID 58904611, compound

HRID 1292843Notes

Reaction equation

HRID 1292843 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][O:16][C:17](=[O:28])[NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[O:25][CH2:26][CH3:27])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[S:29](Cl)([CH3:32])(=[O:31])=[O:30]>C1COCC1>[CH3:32][S:29]([NH:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][O:16][C:17](=[O:28])[NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[O:25][CH2:26][CH3:27])[CH2:12][CH2:13]2)[CH:5]=[CH:6][CH:7]=1)(=[O:31])=[O:30]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 58904652HCID 58904652, compound

Product 1

HCID 58904611HCID 58904611, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 77 mg (0.2 mmol) of 2-[4-(3-aminophenyl)piperazino]ethyl-N-(2-ethoxyphenyl)carbamate derivative and 56 μl (0.4 mmol, 2 eq) of TEA in 5 ml of THF, 31 μl (0.4 mmol, 2 eq) of mesyl chloride is added. Shaking is carried out at room temperature for about 20 hours. After concentration under reduced pressure, H2O is added and the aqueous phase is extracted with CH2Cl2. After drying on Na2SO4 and concentration of the organic phase, a brown oil is obtained which is purified by column chromatography (eluent AcOEt/petroleum ether 8:2) to produce 61 mg of the expected product as a brown oil (yield: 66%).

Workup

  1. additionis added
  2. concentrationAfter concentration under reduced pressure, H2O
  3. additionis added
  4. extractionthe aqueous phase is extracted with CH2Cl2
  5. customAfter drying on Na2SO4 and concentration of the organic phase
  6. customa brown oil is obtained which
  7. customis purified by column chromatography (eluent AcOEt/petroleum ether 8:2)

Sources & evidence

ORD record
ord-3d67b5bb449742b09aeca48f50dd2d3f
Source dataset
uspto-grants-2007_07
Patent number
US07238693B2

Reaction notes

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