HCID 15285754, compound → HCID 15285755, compound

HRID 129176Notes

Reaction equation

HRID 129176 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]([OH:43])([CH2:37][N:38]1[CH:42]=[N:41][CH:40]=[N:39]1)[C@H:10]([N:12]1[C:16](=[O:17])[N:15]([C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:29][CH2:28][N:27](CC4C=CC=CC=4)[CH2:26][CH2:25]3)=[CH:20][CH:19]=2)[CH:14]=[N:13]1)[CH3:11].[H][H]>C(O)C.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]([OH:43])([CH2:37][N:38]1[CH:42]=[N:41][CH:40]=[N:39]1)[C@H:10]([N:12]1[C:16](=[O:17])[N:15]([C:18]2[CH:19]=[CH:20][C:21]([N:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)=[CH:22][CH:23]=2)[CH:14]=[N:13]1)[CH3:11]

Participants

5

Reactant 2

HCID 15285754HCID 15285754, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15285755HCID 15285755, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 170 mg of compound 21 in 20 ml of ethanol was added 20 mg of 10% Pd-C and the mixture was stirred at room temperature in a hydrogen stream for 9 hours. The catalyst was filtered off and washed with 5 ml of ethanol. The filtrate and the washing were combined and concentrated under reduced pressure to give 144 mg of 2-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-4-[4-(1-piperazinyl)phenyl]-3(2H,4H)-1,2,4-triazolone (Compound 22) as a pale yellow oil.

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with 5 ml of ethanol
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-99be5669876148ba96d836ef8bf96da7
Source dataset
uspto-grants-1995_11
Patent number
US05466820

Reaction notes

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