Potassium Carbonate → 1-{3-Cyclopropyl-2-[2-methyl-4-(3,4,5-trimethyl-pyrazol-1-yl)-phenoxymethyl]-phenyl}-4-methyl-1,4-dihydrotetrazole-5-one

HRID 628478Notes

Reaction equation

HRID 628478 reaction equation
Br[CH2:2][C:3]1[C:8]([CH:9]2[CH2:11][CH2:10]2)=[CH:7][CH:6]=[CH:5][C:4]=1[N:12]1[C:16](=[O:17])[N:15]([CH3:18])[N:14]=[N:13]1.[CH3:19][C:20]1[CH:25]=[C:24]([N:26]2[C:30]([CH3:31])=[C:29]([CH3:32])[C:28]([CH3:33])=[N:27]2)[CH:23]=[CH:22][C:21]=1[OH:34].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH:9]1([C:8]2[C:3]([CH2:2][O:34][C:21]3[CH:22]=[CH:23][C:24]([N:26]4[C:30]([CH3:31])=[C:29]([CH3:32])[C:28]([CH3:33])=[N:27]4)=[CH:25][C:20]=3[CH3:19])=[C:4]([N:12]3[C:16](=[O:17])[N:15]([CH3:18])[N:14]=[N:13]3)[CH:5]=[CH:6][CH:7]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 898757781-(2-Bromomethyl-3-cyclopropylphenyl)-4-methyl-1,4-dihydrotetrazol-5-oneHCID 118236550HCID 118236550, compound

Product 1

HCID 1182714141-{3-Cyclopropyl-2-[2-methyl-4-(3,4,5-trimethyl-pyrazol-1-yl)-phenoxymethyl]-phenyl}-4-methyl-1,4-dihydrotetrazole-5-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(2-bromomethyl-3-cyclopropylphenyl)-4-methyl-1,4-dihydrotetrazole-5-one (described in Reference Preparation example 2) δ0 g, 2-methyl-4-(3,4,5-trimethyl-pyrazol-1-yl)-phenol (described in Reference Preparation example 20) 0.36 g, potassium carbonate 0.29 g and acetonitrile 15 ml was stirred with heating under reflux for seven hours. After cooling to room temperature, the reaction mixture was filtered, and the filtrate was then concentrated. The resulting residue was subjected to a silica gel column chromatography to give 1-{3-cyclopropyl-2-[2-methyl-4-(3,4,5-trimethyl-pyrazol-1-yl)-phenoxymethyl]-phenyl}-4-methyl-1,4-dihydrotetrazole-5-one (hereinafter, referred to as “Present compound 2”) δ1 g.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for seven hours
  3. filtrationthe reaction mixture was filtered
  4. concentrationthe filtrate was then concentrated

Sources & evidence

ORD record
ord-78f7951acee647c8b8e591312ded0054
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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