Acetic Acid → HCID 18914268, compound

HRID 1292400Notes

Reaction equation

HRID 1292400 reaction equation
C([N:8]([CH2:24][CH2:25][C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([NH:35][C:36]([N:38]([CH3:40])[CH3:39])=[O:37])[CH:33]=2)[NH:28][C:27]=1[C:41]1[CH:46]=[C:45]([CH3:47])[CH:44]=[C:43]([CH3:48])[CH:42]=1)[CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])=[CH:15][CH:14]=1)C1C=CC=CC=1.C(O)(=O)C.[H][H]>O1CCCC1.CO.[OH-].[OH-].[Pd+2].O>[CH3:48][C:43]1[CH:42]=[C:41]([C:27]2[NH:28][C:29]3[C:34]([C:26]=2[CH2:25][CH2:24][NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])=[CH:17][CH:18]=2)=[CH:33][C:32]([NH:35][C:36]([N:38]([CH3:39])[CH3:40])=[O:37])=[CH:31][CH:30]=3)[CH:46]=[C:45]([CH3:47])[CH:44]=1

Participants

8

Reactant 3

HCID 176Acetic AcidHCID 18914265HCID 18914265, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18914268HCID 18914268, compound

Reagents, catalysts & solvents 4

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of N-{4-[4-(benzyl-{2-[2-(3,5-dimethylphenyl)-5-(3,3-dimethylureido)-1H-indol-3-yl]ethyl}amino)butyl]phenyl}methanesulfonamide (17 mg in a mixture of 4 mL tetrahydrofuran and 1.5 mL methanol) was added 7 mg of 10% palladium hydroxide on carbon catalyst followed by acetic acid (0.020 mL of a 30% solution in water). The reaction flask was fitted with a hydrogen balloon, evacuated and recharged with hydrogen (3 times) and stirred at room temperature. After 45 minutes the reaction was flushed with nitrogen, filtered over diatomaceous earth and concentrated in vacuo. Purification by flash chromatography (methylene chloride:methanol:ammonium hydroxide, 91:9:1) gave the title compound (14.5 mg). m/e=576 (M+H)

Workup

  1. customevacuated
  2. customAfter 45 minutes the reaction was flushed with nitrogen
  3. filtrationfiltered over diatomaceous earth
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography (methylene chloride:methanol:ammonium hydroxide, 91:9:1)

Sources & evidence

ORD record
ord-3120295ebde447f0ac331ce2839b512d
Source dataset
uspto-grants-1998_05
Patent number
US05756507

Reaction notes

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