HCID 178418361, compound → HCID 178449101, compound

HRID 2410252Notes

Reaction equation

HRID 2410252 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[C:14]([O:35]CC3C=CC=CC=3)=[CH:15][C:16]([O:27]CC3C=CC=CC=3)=[C:17]([CH:26]=2)[C:18]([N:20]([CH3:25])[CH2:21][CH2:22][CH2:23][CH3:24])=[O:19])=[N:11][N:10]=[C:9]1[OH:43].[H][H]>C1COCC1.[Pd]>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[C:14]([OH:35])=[CH:15][C:16]([OH:27])=[C:17]([CH:26]=2)[C:18]([N:20]([CH3:25])[CH2:21][CH2:22][CH2:23][CH3:24])=[O:19])=[N:11][N:10]=[C:9]1[OH:43]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178449102HCID 178449102, compound

Product 1

HCID 178449101HCID 178449101, compoundYield 97.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.1 kg of 5-[4-(2-methylphenyl)-3-hydroxy-4H-1,2,4-triazol-5-yl]-2,4-bisbenzyloxy-N-methyl-N-butylbenzamide, 5% Pd/C (50.5% of water) and 85 l of hydrogen in 10 l of THF is treated at 23° C. for 7 h in an autoclave. The resultant solution is subsequently evaporated and crystallised from ethanol, giving 738 g (95%) of 5-[4-(2-methylphenyl)-3-hydroxy-4H-1,2,4-triazol-5-yl]-2,4-dihydroxy-N-methyl-N-butylbenzamide (“C1”); MW 396.5.

Workup

  1. customThe resultant solution is subsequently evaporated
  2. customcrystallised from ethanol

Sources & evidence

ORD record
ord-52f8325a0f514681966c3e95ef0b8589
Source dataset
uspto-grants-2014_08
Patent number
US08816070B2

Reaction notes

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