HCID 19898936, compound → HCID 19898935, compound

HRID 1196546Notes

Reaction equation

HRID 1196546 reaction equation
C([N:8]([C:13]1[CH:18]=[CH:17][C:16]([CH:19]([OH:36])[CH2:20][N:21]([CH2:23][CH2:24][N:25]2[N:34]=[CH:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]2=[O:35])[CH3:22])=[CH:15][CH:14]=1)[S:9]([CH3:12])(=[O:11])=[O:10])C1C=CC=CC=1>C(O)C.C(OCC)C.[Pd]>[CH3:12][S:9]([NH:8][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([OH:36])[CH2:20][N:21]([CH2:23][CH2:24][N:25]2[N:34]=[CH:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]2=[O:35])[CH3:22])=[CH:15][CH:14]=1)(=[O:10])=[O:11]

Participants

5

Reactant 1

HCID 19898936HCID 19898936, compound

Product 1

HCID 19898935HCID 19898935, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

N-[2-(4-{N-Benzylmethanesulphonamido}phenyl)-2-hydroxyethyl]-N-methyl-2-(phthalazin-1-on-2yl)ethylamine (0.4 g--as solvate from part D) in ethanol (50 ml) containing 5% Pd/C (0.1 g) was stirred under a hydrogen atmosphere (50 p.s.i.) at 50° for 18 hours. The reaction mixture was then filtered and the ethanol removed. The residue was dissolved in methylene chloride and washed three times with sodium bicarbonate solution and three times with brine. The organic layer was dried and evaporated to give an oil which was purified by column chromatography on silica, "Kieselgel 60" (Merck, Trade Mark), eluting with methylene chloride containing methanol (0% up to 2%). The appropriate fractions were combined and evaporated to give an oil which solidified after stirring for 14 hours in diethyl ether, filtration giving the title compound, 0.11 g, m.p. 134°-137°.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. customthe ethanol removed
  3. dissolutionThe residue was dissolved in methylene chloride
  4. washwashed three times with sodium bicarbonate solution and three times with brine
  5. customThe organic layer was dried
  6. customevaporated
  7. customto give an oil which
  8. customwas purified by column chromatography on silica, "Kieselgel 60" (Merck, Trade Mark)
  9. washeluting with methylene chloride
  10. additioncontaining methanol (0% up to 2%)
  11. customevaporated
  12. customto give an oil which
  13. filtrationfiltration

Sources & evidence

ORD record
ord-f0cd9d3f483f48b5823b05a71cf25507
Source dataset
uspto-grants-1992_05
Patent number
US05114952

Reaction notes

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