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 1532376Notes

Reaction equation

HRID 1532376 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-edcc039e39e946119c33a4699a8de051
Source dataset
uspto-grants-2001_03
Patent number
US06200957B1

Reaction notes

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