Hydrochloric Acid → Isopropyl 4-[1-(2-chloropyridin-3-yl)-5-methyl-1H-[1,2,3]triazol-4-yl]-piperazine-1-carboxylate

HRID 2267173Notes

Reaction equation

HRID 2267173 reaction equation
Cl.[Cl:2][C:3]1[C:8]([N:9]2[C:13]([CH3:14])=[C:12]([N:15]3[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24](C)([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]3)[N:11]=[N:10]2)=[CH:7][CH:6]=[CH:5][N:4]=1>O1CCOCC1>[Cl:2][C:3]1[C:8]([N:9]2[C:13]([CH3:14])=[C:12]([N:15]3[CH2:20][CH2:19][N:18]([C:21]([O:23][CH:24]([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]3)[N:11]=[N:10]2)=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58945868HCID 58945868, compound

Product 1

HCID 58945835Isopropyl 4-[1-(2-chloropyridin-3-yl)-5-methyl-1H-[1,2,3]triazol-4-yl]-piperazine-1-carboxylateYield 69.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4N Hydrochloric acid solution in dioxane (10 ml) was added to 3 mg of tert-Butyl 4-[1-(2-chloropyridin-3-yl)-5-methyl-1H-[1,2,3]triazol-4-yl)-piperazine-1-carboxylate prepared in Example 34, the mixture was stirred at room temperature for 3 hours, the solvent was evaporated in vacuo, the residue was dissolved in 1 ml of chloroform and, in a nitrogen atmosphere, 0.03 ml of isopropyl chloroformate and 0.06 ml of triethylamine were added thereto and the mixture was stirred at room temperature for 2 hours. After the solvent was evaporated in vacuo, the resulting residue was purified by a preparative thin-layer silica gel chromatography (chloroform:methanol=9:1) to give 2 mg of the title compound as a white solid.

Workup

  1. customthe solvent was evaporated in vacuo
  2. dissolutionthe residue was dissolved in 1 ml of chloroform and, in a nitrogen atmosphere, 0.03 ml of isopropyl chloroformate and 0.06 ml of triethylamine
  3. additionwere added
  4. stirringthe mixture was stirred at room temperature for 2 hours
  5. customAfter the solvent was evaporated in vacuo
  6. customthe resulting residue was purified by a preparative thin-layer silica gel chromatography (chloroform:methanol=9:1)

Sources & evidence

ORD record
ord-60c841fa101d4456a166fb4668b4b416
Source dataset
uspto-grants-2010_12
Patent number
US07858800B2

Reaction notes

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