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

HRID 628479Notes

Reaction equation

HRID 628479 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]([C:26]2[CH:30]=[CH:29][N:28]([CH3:31])[N:27]=2)[CH:23]=[CH:22][C:21]=1[OH:32].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH:9]1([C:8]2[C:3]([CH2:2][O:32][C:21]3[CH:22]=[CH:23][C:24]([C:26]4[CH:30]=[CH:29][N:28]([CH3:31])[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 1367563942-methyl-4-(1-methyl-1H-pyrazol-3-yl)-phenol

Product 1

HCID 1179786221-{3-cyclopropyl-2-[2-methyl-4-(1-methyl-1H-pyrazol-3-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 0.30 g, 2-methyl-4-(1-methyl-1H-pyrazol-3-yl)-phenol (described in Reference Preparation example 29) 0.18 g, potassium carbonate 0.18 g and acetonitrile 10 ml was stirred with heating under reflux for four 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-(1-methyl-1H-pyrazol-3-yl)-phenoxymethyl]-phenyl}-4-methyl-1,4-dihydrotetrazole-5-one (hereinafter, referred to as “Present compound 12”) 0.22 g.

Workup

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

Sources & evidence

ORD record
ord-4ee0e919fac2455e97a0f80549c52c3b
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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