Potassium Carbonate → 7-(4-chlorophenyl)-2-((2-(hydroxymethyl)-6-(trifluoromethyl)pyridin-3-yl)methyl)-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

HRID 2101338Notes

Reaction equation

HRID 2101338 reaction equation
C([O:4][CH2:5][C:6]1[C:11]([CH2:12][N:13]2[C:34](=[O:35])[N:16]3[CH:17]=[CH:18][C:19]([C:27]4[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=4)=[C:20]([C:21]4[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=4)[C:15]3=[N:14]2)=[CH:10][CH:9]=[C:8]([C:36]([F:39])([F:38])[F:37])[N:7]=1)(=O)C.C([O-])([O-])=O.[K+].[K+]>CO>[Cl:33][C:30]1[CH:29]=[CH:28][C:27]([C:19]2[CH:18]=[CH:17][N:16]3[C:34](=[O:35])[N:13]([CH2:12][C:11]4[C:6]([CH2:5][OH:4])=[N:7][C:8]([C:36]([F:38])([F:39])[F:37])=[CH:9][CH:10]=4)[N:14]=[C:15]3[C:20]=2[C:21]2[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=2)=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 16004843(3-((7-(4-chlorophenyl)-3-oxo-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-2(3H)-yl)methyl)-6-(trifluoromethyl)pyridin-2-yl)methyl acetate

Product 1

HCID 160048747-(4-chlorophenyl)-2-((2-(hydroxymethyl)-6-(trifluoromethyl)pyridin-3-yl)methyl)-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-oneYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (3-((7-(4-chlorophenyl)-3-oxo-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-2(3H)-yl)methyl)-6-(trifluoromethyl)pyridin-2-yl)methyl acetate (220 mg, 0.397 mmol) and 1.0 M aqueous K2CO3 solution (3.1 mL, 3.1 mmol) in methanol (7 mL) was stirred at room temperature for 30 min, then concentrated under reduced pressure. The crude product was purified using a silica gel cartridge (12 g) eluted with a gradient of ethyl acetate (50-100%) in hexanes to afford 156 mg (77%) of the title compound as a yellow foam. A portion of the product (110 mg) was further purified using preparative reverse phase HPLC (Phenomenex Luna 5 μm C-18 21.2×100 mm column eluted with a linear gradient of 50% to 100% B over 8 min (A=90% water, 10% methanol and B=90% methanol, 10% water) with flow rate at 20 mL/min and UV detection at 220 nm). The desired fractions were concentrated under reduced pressure. The residue was dissolved in acetonitrile, frozen and lyophilized to afford 97 mg of the title compound as a light yellow powder. HPLC/MS: retention time=2.67 min, [M+H]+=512.0.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude product was purified
  3. washeluted with a gradient of ethyl acetate (50-100%) in hexanes

Sources & evidence

ORD record
ord-fd6d42bbac184706aa6a3f671769fb5e
Source dataset
uspto-grants-2009_08
Patent number
US07572808B2

Reaction notes

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