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

HRID 628480Notes

Reaction equation

HRID 628480 reaction equation
[CH3:1][C:2]1[CH:28]=[C:27]([N:29]2[C:33]([CH3:34])=[C:32]([CH3:35])[C:31]([CH3:36])=[N:30]2)[CH:26]=[CH:25][C:3]=1[O:4][CH2:5][C:6]1[C:11]([C:12]#[C:13][Si](C)(C)C)=[CH:10][CH:9]=[CH:8][C:7]=1[N:18]1[C:22](=[O:23])[N:21]([CH3:24])[N:20]=[N:19]1.C(=O)([O-])[O-].[K+].[K+].C(Cl)(Cl)Cl>CO>[C:12]([C:11]1[C:6]([CH2:5][O:4][C:3]2[CH:25]=[CH:26][C:27]([N:29]3[C:33]([CH3:34])=[C:32]([CH3:35])[C:31]([CH3:36])=[N:30]3)=[CH:28][C:2]=2[CH3:1])=[C:7]([N:18]2[C:22](=[O:23])[N:21]([CH3:24])[N:20]=[N:19]2)[CH:8]=[CH:9][CH:10]=1)#[CH:13]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 11430Potassium CarbonateHCID 1238857971-{2-(2-Methyl-4-(3,4,5-trimethyl-pyrazol-1-yl)-phenoxymethyl)-3-trimethylsilylethynyl-phenyl}-4-methyl-1,4-dihydrotetrazole-5-one

Product 1

HCID 1182904411-{3-Ethynyl-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 887MethanolSolvent

Procedure

A mixture of 1-{2-(2-methyl-4-(3,4,5-trimethyl-pyrazol-1-yl)-phenoxymethyl)-3-trimethylsilylethynyl-phenyl}-4-methyl-1,4-dihydrotetrazole-5-one (described in Reference Preparation example 71) 0.2 g, potassium carbonate 0.7 g, chloroform 5 ml and methanol 5 ml was stirred at room temperature for three hours, and then the resulting mixture was heated to 60° C. and was stirred for three hours. The reaction mixture was filtered, and the filtrate was then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 1-{3-ethynyl-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 20”) 0.07 g.

Workup

  1. temperaturethe resulting mixture was heated to 60° C.
  2. stirringwas stirred for three hours
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-f5611df632f54f908bc97bbc57ecb998
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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