Hydrochloric Acid → HCID 178497405, compound

HRID 1487987Notes

Reaction equation

HRID 1487987 reaction equation
C([N:8]1[C:12]([O:13][CH3:14])=[N:11][N:10]=[C:9]1[C:15]1[C:16]([CH:26]2[CH2:28][CH2:27]2)=[CH:17][C:18]([CH3:25])=[C:19]([CH:24]=1)[C:20]([O:22][CH3:23])=[O:21])C1C=CC=CC=1.Cl.[H][H]>[Pd].CO>[CH:26]1([C:16]2[C:15]([C:9]3[NH:8][C:12]([O:13][CH3:14])=[N:11][N:10]=3)=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([CH3:25])[CH:17]=2)[CH2:28][CH2:27]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 90029805Methyl 5-(4-benzyl-5-methoxy-4H-1,2,4-triazol-3-yl)-4-cyclopropyl-2-methylbenzoate2×HCID 178418361HCID 178418361, compound

Product 1

HCID 178497405HCID 178497405, compoundYield 71.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A flask containing methyl 5-(4-benzyl-5-methoxy-4H-1,2,4-triazol-3-yl)-4-cyclopropyl-2-methylbenzoate (compound 91.4, 0.55 g, 1.46 mmol) and Pd/C (10%, 0.25 g) was purged with nitrogen, then MeOH (10 mL) and HCl (4 M in dioxane, 37 μL, 0.15 mmol) were carefully added. The system was then charged with hydrogen and the mixture was stirred at room temperature for 3 hours. Upon completion, the system was purged with nitrogen, then the mixture was neutralized with a few drops of NH4OH and filtered through Celite®. The filtrate was concentrated under reduced pressure and the residue was purified using prep-TLC (hexanes:EtOAc 1:1) to yield 0.3 g (71%) of the title compound as a clear oil. m/z (ES+) 288 (M+H)+.

Workup

  1. customwas purged with nitrogen
  2. customUpon completion, the system was purged with nitrogen
  3. filtrationfiltered through Celite®
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified

Sources & evidence

ORD record
ord-f528d65f4be94544a14612b43116bee3
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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