HCID 58945841, compound → HCID 58945866, compound

HRID 2267136Notes

Reaction equation

HRID 2267136 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([CH2:13][O:14][CH3:15])=[C:11]([C:16]2[CH2:17][CH2:18][N:19]([C:22]([O:24][C:25](C)([CH3:27])[CH3:26])=[O:23])[CH2:20][CH:21]=2)[N:10]=[N:9]1>Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([CH2:13][O:14][CH3:15])=[C:11]([C:16]2[CH2:17][CH2:18][N:19]([C:22]([O:24][CH:25]([CH3:27])[CH3:26])=[O:23])[CH2:20][CH:21]=2)[N:10]=[N:9]1

Participants

3

Reactant 1

HCID 58945841HCID 58945841, compound

Product 1

HCID 58945866HCID 58945866, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

tert-Butyl 4-[1-(2-fluorophenyl)-5-methoxymethyl-1H-[1,2,3]triazol-4-yl]-1,2,3,6-tetrahydropyridine-1-carboxylate (5.4 mg) prepared in the above 4) was dissolved in 2.0 ml of a 10% methanolic solution of hydrochloric acid followed by stirring at room temperature for 30 minutes. The solvent was evaporated in vacuo followed, without purification, by dissolving in 0.5 ml of pyridine and 0.02 ml of isopropyl chloroformate was added to the solution followed by stirring for 1 hour. A saturated aqueous solution of ammonium chloride was added to the reaction solution, the mixture was extracted with ethyl acetate, the extract was dried over sodium sulfate and the solvent was evaporated in vacuo. The resulting residue was separate and purified by a thin-layer chromatography (ethyl acetate/hexane=1/2) to give 4.27 mg of the title compound as a white solid.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customfollowed, without purification
  3. dissolutionby dissolving in 0.5 ml of pyridine
  4. addition0.02 ml of isopropyl chloroformate was added to the solution
  5. stirringby stirring for 1 hour
  6. additionA saturated aqueous solution of ammonium chloride was added to the reaction solution
  7. extractionthe mixture was extracted with ethyl acetate
  8. dry with materialthe extract was dried over sodium sulfate
  9. customthe solvent was evaporated in vacuo
  10. customThe resulting residue was separate
  11. custompurified by a thin-layer chromatography (ethyl acetate/hexane=1/2)

Sources & evidence

ORD record
ord-c06aea307ed5484dac4906969dc7928c
Source dataset
uspto-grants-2010_12
Patent number
US07858800B2

Reaction notes

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