Acetic Acid → 1-{2-(3,5-dimethylphenyl)-3-[2-(4-pyridin-3-yl-butylamino)ethyl]-1H-indol-5-yl}4-methyl-1,4-dihydrotetrazol-5-one

HRID 1956530Notes

Reaction equation

HRID 1956530 reaction equation
C([N:8]([CH2:35][CH2:36][CH2:37][CH2:38][C:39]1[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=1)[CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([N:20]3[C:24](=[O:25])[N:23]([CH3:26])[N:22]=[N:21]3)[CH:18]=2)[NH:13][C:12]=1[C:27]1[CH:32]=[C:31]([CH3:33])[CH:30]=[C:29]([CH3:34])[CH:28]=1)C1C=CC=CC=1.C(O)(=O)C.[H][H]>[OH-].[OH-].[Pd+2].O>[CH3:34][C:29]1[CH:28]=[C:27]([C:12]2[NH:13][C:14]3[C:19]([C:11]=2[CH2:10][CH2:9][NH:8][CH2:35][CH2:36][CH2:37][CH2:38][C:39]2[CH:40]=[N:41][CH:42]=[CH:43][CH:44]=2)=[CH:18][C:17]([N:20]2[C:24](=[O:25])[N:23]([CH3:26])[N:22]=[N:21]2)=[CH:16][CH:15]=3)[CH:32]=[C:31]([CH3:33])[CH:30]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 212498931-[3-{2-[benzyl-(4-pyridin-3-yl-butyl)amino]ethyl}2-(3,5-dimethylphenyl)-1H-indol-5-yl]-4-methyl-1,4-dihydrotetrazol-5-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 98058151-{2-(3,5-dimethylphenyl)-3-[2-(4-pyridin-3-yl-butylamino)ethyl]-1H-indol-5-yl}4-methyl-1,4-dihydrotetrazol-5-oneYield 94.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 962WaterSolvent

Procedure

To a stirred solution of 1-[3-{2-[benzyl-(4-pyridin-3-yl-butyl)amino]ethyl }-2-(3,5-dimethylphenyl)-1H-indol-5-yl] -4-methyl-1,4-dihydrotetrazol-5-one (20 mg in 4 mL methanol) was added 15 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 30 minutes the reaction was flushed with nitrogen, filtered over diatomaceous earth and concentrated in vacuo. Purification by flash chromatography (methylene chloride:methanol:ammonium hydroxide, 90:6.5:1) gave the title compound (16 mg). m/e=496 (M+H)

Workup

  1. customevacuated
  2. customAfter 30 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, 90:6.5:1)

Sources & evidence

ORD record
ord-5bb373ec35304cf096ab5e083c6e4df2
Source dataset
uspto-grants-1998_07
Patent number
US05780437

Reaction notes

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