Benzyl 3-(5-cyano-4-(2,6-difluorophenyl)-N-isopropyl-1H-1,2,3-triazole-1-carboxamido)benzoate → 3-(5-cyano-4-(2,6-difluorophenyl)-N-isopropyl-1H-1,2,3-triazole-1-carboxamido)benzoic acid

HRID 2097675Notes

Reaction equation

HRID 2097675 reaction equation
[C:1]([C:3]1[N:7]([C:8]([N:10]([C:14]2[CH:15]=[C:16]([CH:27]=[CH:28][CH:29]=2)[C:17]([O:19]CC2C=CC=CC=2)=[O:18])[CH:11]([CH3:13])[CH3:12])=[O:9])[N:6]=[N:5][C:4]=1[C:30]1[C:35]([F:36])=[CH:34][CH:33]=[CH:32][C:31]=1[F:37])#[N:2].[H][H]>CO.[Pd]>[C:1]([C:3]1[N:7]([C:8]([N:10]([C:14]2[CH:15]=[C:16]([CH:27]=[CH:28][CH:29]=2)[C:17]([OH:19])=[O:18])[CH:11]([CH3:13])[CH3:12])=[O:9])[N:6]=[N:5][C:4]=1[C:30]1[C:31]([F:37])=[CH:32][CH:33]=[CH:34][C:35]=1[F:36])#[N:2]

Participants

5

Reactant 2

HCID 58501889Benzyl 3-(5-cyano-4-(2,6-difluorophenyl)-N-isopropyl-1H-1,2,3-triazole-1-carboxamido)benzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 545887653-(5-cyano-4-(2,6-difluorophenyl)-N-isopropyl-1H-1,2,3-triazole-1-carboxamido)benzoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of benzyl ester (6) (1.0 equiv) in methanol (0.1 M) under argon was added 5% Pd/C (0.1 equiv) and the inert atmosphere was replaced with hydrogen. The resulting mixture was stirred at rt for 30 min, filtered through a pad of Celite with aid of methanol and the resulting filtrate concentrated in vacuo. The residue was purified by preparative HPLC (0.1% formic acid in acetonitrile/water) to afford 3-(5-cyano-4-(2,6-difluorophenyl)-N-isopropyl-1H-1,2,3-triazole-1-carboxamido)benzoic acid (7) as a lyophilized powder.

Workup

  1. filtrationfiltered through a pad of Celite with aid of methanol
  2. concentrationthe resulting filtrate concentrated in vacuo
  3. customThe residue was purified by preparative HPLC (0.1% formic acid in acetonitrile/water)

Sources & evidence

ORD record
ord-d0efb327d0cd4d748b6e112bb6564f83
Source dataset
uspto-grants-2013_05
Patent number
US08450350B2

Reaction notes

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