(E)-2-(2-(5-Methyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)vinyl)-[1,2,4]triazolo[5,1-f][1,6]naphthyridine → 2-(2-(5-Methyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)ethyl)-5,6-dihydro-[1,2,4]triazolo[5,1-f][1,6]naphthyridine

HRID 1615657Notes

Reaction equation

HRID 1615657 reaction equation
[CH3:1][C:2]1[N:7]2[N:8]=[C:9](/[CH:11]=[CH:12]/[C:13]3[N:25]=[C:16]4[C:17]5[CH:18]=[CH:19][CH:20]=[N:21][C:22]=5[CH:23]=[CH:24][N:15]4[N:14]=3)[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1>CO.[OH-].[Na+].[Pd]>[CH3:1][C:2]1[N:7]2[N:8]=[C:9]([CH2:11][CH2:12][C:13]3[N:25]=[C:16]4[C:17]5[CH:18]=[CH:19][CH:20]=[N:21][C:22]=5[CH2:23][CH2:24][N:15]4[N:14]=3)[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 68089402(E)-2-(2-(5-Methyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)vinyl)-[1,2,4]triazolo[5,1-f][1,6]naphthyridine

Product 1

HCID 680894732-(2-(5-Methyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)ethyl)-5,6-dihydro-[1,2,4]triazolo[5,1-f][1,6]naphthyridine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of (E)-2-(2-(5-methyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)vinyl)-[1,2,4]triazolo[5,1-f][1,6]naphthyridine (17 mg, 0.52 mmol) in MeOH (3 mL) and aqueous NaOH (1 N, 1 mL) was added 10% Pd/C (17 mg) under a nitrogen atmosphere. The reaction vessel was degassed for three times, followed by treatment with H2 for 1 h at room temperature. The mixture was then submitted for prep-HPLC purification to give a free base of the title compound as a white solid. The solid was triturated with a solution of HCl (gas) in EtOAc (2 mL) to afford the di-HCl salt of the title compound as a yellow solid (7.83 mg, yield 37%). ESI MS: m/z 332 [M+H]+.

Workup

  1. customThe reaction vessel was degassed for three times
  2. customThe mixture was then submitted for prep-HPLC purification

Sources & evidence

ORD record
ord-968533eedd5c4e31a760b93725ef6352
Source dataset
uspto-grants-2014_07
Patent number
US08765760B2

Reaction notes

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