Acetic Acid → HCID 59944552, compound

HRID 1531548Notes

Reaction equation

HRID 1531548 reaction equation
C([N:8]([CH2:36][CH2:37][CH2:38][CH2:39][C:40]1[CH:45]=[CH:44][C:43]([NH:46][S:47]([CH3:50])(=[O:49])=[O:48])=[CH:42][CH:41]=1)[CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([NH:20][C:21]([N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[O:22])[CH:18]=2)[NH:13][C:12]=1[C:28]1[CH:33]=[C:32]([CH3:34])[CH:31]=[C:30]([CH3:35])[CH:29]=1)C1C=CC=CC=1.C(O)(=O)C.[H][H]>O1CCCC1.CO.[OH-].[OH-].[Pd+2].O>[CH3:34][C:32]1[CH:33]=[C:28]([C:12]2[NH:13][C:14]3[C:19]([C:11]=2[CH2:10][CH2:9][NH:8][CH2:36][CH2:37][CH2:38][CH2:39][C:40]2[CH:45]=[CH:44][C:43]([NH:46][S:47]([CH3:50])(=[O:49])=[O:48])=[CH:42][CH:41]=2)=[CH:18][C:17]([NH:20][C:21]([N:23]2[CH2:24][CH2:25][CH2:26][CH2:27]2)=[O:22])=[CH:16][CH:15]=3)[CH:29]=[C:30]([CH3:35])[CH:31]=1

Participants

8

Reactant 3

HCID 176Acetic AcidHCID 53781390HCID 53781390, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59944552HCID 59944552, compound

Reagents, catalysts & solvents 4

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of pyrrolidine-1-carboxylic acid [3-(2-{benzyl-[4-(4-methanesulfonylaminophenyl)butyl]amino}ethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-amide (16 mg in a mixture of 1 mL tetrahydrofuran and 3 mL methanol) was added 15 mg of 10% palladium hydroxide on carbon catalyst followed by acetic acid (0.015 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 25 minutes the reaction was flushed with nitrogen, filtered over diatomaceous earth and concentrated in vacuo. Purification by flash chromatography (methylene chloride:methanol:ammonium hydroxide, 90:8:1) gave the title compound (14 mg). m/e=602 (M+H)

Workup

  1. customevacuated
  2. customAfter 25 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, 90:8:1)

Sources & evidence

ORD record
ord-3a0f95cdcb5945ff981ab8598f904fed
Source dataset
uspto-grants-2001_03
Patent number
US06197975B1

Reaction notes

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