Ethylamine hydrochloride → HCID 58244204, compound

HRID 389160Notes

Reaction equation

HRID 389160 reaction equation
[Cl:1][C:2]1[CH:23]=[C:22]([F:24])[C:5]([O:6][C:7]([C:10]2O[C:13]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH2:21])[CH:16]=3)=[N:12][N:11]=2)([CH3:9])[CH3:8])=[C:4]([F:25])[CH:3]=1.Cl.[CH2:27]([NH2:29])[CH3:28]>CO>[Cl:1][C:2]1[CH:23]=[C:22]([F:24])[C:5]([O:6][C:7]([C:10]2[N:29]([CH2:27][CH3:28])[C:13]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH2:21])[CH:16]=3)=[N:12][N:11]=2)([CH3:9])[CH3:8])=[C:4]([F:25])[CH:3]=1

Participants

4

Reactant 2

HCID 11198Ethylamine hydrochlorideHCID 58244147HCID 58244147, compound

Product 1

HCID 58244204HCID 58244204, compoundYield 2.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methanol was added to a mixture of 4-{5-[1-(4-chloro-2,6-difluorophenoxy)-1-methylethyl]-1,3,4-oxadiazol-2-yl}pyridin-2-amine (258 mg) and ethylamine hydrochloride (1.0 g), followed by homogenizing. The solvent was evaporated under reduced pressure, followed by melting at 150° C. for 7 hours. The reaction solution was cooled to room temperature, equivalent amounts of water and saturated brine were added thereto, followed by extraction with ethyl acetate, the organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (chloroform:methanol), and the resulting solid was washed with diisopropylether, to obtain, as an ocher solid, 4-{5-[1-(4-chloro-2,6-difluorophenoxy)-1-methylethyl]-4-ethyl-4H-1,2,4-triazol-3-yl}pyridin-2-amine (8.0 mg).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionequivalent amounts of water and saturated brine were added
  3. extractionfollowed by extraction with ethyl acetate
  4. washthe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (chloroform:methanol)
  8. washthe resulting solid was washed with diisopropylether

Sources & evidence

ORD record
ord-e2c4aae60914416480f9d564557aef7f
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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