Pyridinium chloride → 4-[5-(2-Oxo-1,2-dihydro-pyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino]-N-pyridin-3-ylmethyl-benzamide

HRID 1011273Notes

Reaction equation

HRID 1011273 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([C:9]2[N:14]3[N:15]=[CH:16][N:17]=[C:13]3[C:12]([NH:18][C:19]3[CH:34]=[CH:33][C:22]([C:23]([NH:25][CH2:26][C:27]4[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=4)=[O:24])=[CH:21][CH:20]=3)=[CH:11][CH:10]=2)[CH:6]=[CH:5][N:4]=1.Cl.N1C=CC=CC=1>O>[O:2]=[C:3]1[CH:8]=[C:7]([C:9]2[N:14]3[N:15]=[CH:16][N:17]=[C:13]3[C:12]([NH:18][C:19]3[CH:20]=[CH:21][C:22]([C:23]([NH:25][CH2:26][C:27]4[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=4)=[O:24])=[CH:33][CH:34]=3)=[CH:11][CH:10]=2)[CH:6]=[CH:5][NH:4]1

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 576643794-[5-(2-Methoxy-pyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino]-N-pyridin-3-ylmethyl-benzamide

Product 1

HCID 249470064-[5-(2-Oxo-1,2-dihydro-pyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino]-N-pyridin-3-ylmethyl-benzamideYield 62.8%

Reagents, catalysts & solvents 1

HCID 962WaterCatalyst

Procedure

4-[5-(2-Methoxy-pyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino]-N-pyridin-3-ylmethyl-benzamide (46 mg, 51 μmol) is treated in a sealed tube with pyridine hydrochloride (153 mg, 1.32 mmol) and one drop of water at 150° C. for two hours. The reaction mixture is evaporated and the residue purified by flash chromatography (silica gel, dichloromethane/7N NH3 in methanol 96:4 then 85:15) affording the title compound (14 mg) as a solid.

Workup

  1. customThe reaction mixture is evaporated
  2. customthe residue purified by flash chromatography (silica gel, dichloromethane/7N NH3 in methanol 96:4

Sources & evidence

ORD record
ord-3baea2c21cbd4c59bfa3d2b5ec191f20
Source dataset
uspto-grants-2011_07
Patent number
US07977352B2

Reaction notes

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