Pyridine → HCID 15022943, compound

HRID 893522Notes

Reaction equation

HRID 893522 reaction equation
[Cl:1][CH:2]([CH2:6][C:7]1[CH:12]=[C:11]([N:13]2[C:17](=[O:18])[N:16]([CH:19]([F:21])[F:20])[C:15]([CH3:22])=[N:14]2)[C:10]([Cl:23])=[CH:9][C:8]=1[Cl:24])[C:3]([OH:5])=O.S(Cl)(Cl)=O.Cl.[CH3:30][NH:31][O:32][CH3:33].N1C=CC=CC=1>O1CCCC1.C(OCC)C>[CH3:30][N:31]([O:32][CH3:33])[C:3](=[O:5])[CH:2]([Cl:1])[CH2:6][C:7]1[CH:12]=[C:11]([N:13]2[C:17](=[O:18])[N:16]([CH:19]([F:21])[F:20])[C:15]([CH3:22])=[N:14]2)[C:10]([Cl:23])=[CH:9][C:8]=1[Cl:24]

Participants

7

Reactant 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 15022941HCID 15022941, compound2×

Product 1

HCID 15022943HCID 15022943, compoundYield 64.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.50 g (0.0013 mole) of 2-chloro-3[2,4-dichloro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenyl]propionic acid (Compound 2) and 5 mL of thionyl chloride was stirred at reflux for three hours. The mixture was cooled, and excess thionyl chloride was removed by distillation under reduced pressure leaving a residue. The residue was added to a cold solution of 0.13 g (0.0014 mole) of N,O-dimethylhydroxylamine hydrochloride and 0.11 g (0.0014 mole) of pyridine in 20 mL of tetrahydrofuran. The resultant mixture was stirred at room temperature for approximately 18 hours. The reaction mixture was diluted with diethyl ether and was washed in succession with a 1N hydrochloric acid solution, an aqueous 10% sodium hydroxide solution, water, and an aqueous saturated sodium chloride solution. The washed organic phase was dried over anhydrous magnesium sulfate and was filtered. The filtrate was evaporated under reduced pressure to give 0.37 g of N-methyl-N-methoxy-2-chloro-3-[2,4-dichloro-5 -(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1yl)phenyl]propionamide as an oil, Compound 22 of Table 1.

Workup

  1. temperatureat reflux for three hours
  2. temperatureThe mixture was cooled
  3. customexcess thionyl chloride was removed by distillation under reduced pressure
  4. customleaving a residue
  5. washwas washed in succession with a 1N hydrochloric acid solution
  6. dry with materialThe washed organic phase was dried over anhydrous magnesium sulfate
  7. filtrationwas filtered
  8. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9bf5e79080394107ac5fc9144a89d6a6
Source dataset
uspto-grants-1992_06
Patent number
US05125958

Reaction notes

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