Pyridine → HCID 131735354, compound

HRID 628553Notes

Reaction equation

HRID 628553 reaction equation
[CH:1]1([C:4]2[C:5]([CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([N:25]4[C:29]([CH3:30])=[C:28]([CH:31]=O)[C:27]([CH3:33])=[N:26]4)=[CH:21][C:20]=3[CH3:34])=[C:6]([N:10]3[C:14](=[O:15])[N:13]([CH3:16])[N:12]=[N:11]3)[CH:7]=[CH:8][CH:9]=2)[CH2:3][CH2:2]1.C(Cl)(Cl)Cl.Cl.[NH2:40][OH:41].N1C=CC=CC=1>O>[CH:1]1([C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([N:10]3[C:14](=[O:15])[N:13]([CH3:16])[N:12]=[N:11]3)[C:5]=2[CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([N:25]3[C:29]([CH3:30])=[C:28]([CH:31]=[N:40][OH:41])[C:27]([CH3:33])=[N:26]3)=[CH:21][C:20]=2[CH3:34])[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6212ChloroformHCID 443297Hydroxyamine hydrochlorideHCID 118290400HCID 118290400, compound2×

Product 1

HCID 131735354HCID 131735354, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

At room temperature, a mixture of 1-{3-cyclopropyl-2-[2-methyl-4-(3,5-dimethyl-4-formyl-pyrazol-1-yl)-phenoxymethyl]-phenyl}-4-methyl-1,4-dihydrotetrazole-5-one (Present compound 51) 1.7 g, chloroform 20 ml, hydroxylamine hydrochloride salt 0.3 g and pyridine 0.9 g was stirred for twelve hours. To the resulting mixture was added water 20 ml, and the mixture was extracted with chloroform. The organic layer was washed with water and was dried over anhydrous magnesium sulfate, and then was concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 1-{4-[2-Cyclopropyl-6-(4-methyl-5-oxo-4,5-dihydro-tetrazol-1-yl)-benzyloxy]-3-methyl-phenyl}-3,5-dimethyl-1H-pyrazole-4-carbaldehyde oxime 1.4 g.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe organic layer was washed with water
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-a75b14bc9b334034bbe00c392d8b683f
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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