Hydrogen Peroxide → HCID 58374776, compound

HRID 533177Notes

Reaction equation

HRID 533177 reaction equation
[C:1]([C:3]1[N:8]=[CH:7][C:6]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[N:22]4[N:23]=[C:24]([NH:26][C:27]([CH:29]5[CH2:31][CH2:30]5)=[O:28])[N:25]=[C:21]4[CH:20]=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)=[CH:5][CH:4]=1)#[N:2].C([O-])([O-])=[O:33].[K+].[K+].OO>CS(C)=O>[CH:29]1([C:27]([NH:26][C:24]2[N:25]=[C:21]3[CH:20]=[CH:19][CH:18]=[C:17]([C:14]4[CH:13]=[CH:12][C:11]([O:10][CH2:9][C:6]5[CH:5]=[CH:4][C:3]([C:1]([NH2:2])=[O:33])=[N:8][CH:7]=5)=[CH:16][CH:15]=4)[N:22]3[N:23]=2)=[O:28])[CH2:30][CH2:31]1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 44602526n-(5-(4-((6-Cyanopyridin-3-yl)methoxy)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide

Product 1

HCID 58374776HCID 58374776, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a solution of cyclopropanecarboxylic acid{5-[4-(6-cyano-pyridin-3-ylmethoxy)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide (30 mg, 0.073 mmol, 1 equiv) and K2CO3 (10 mg, 0.073 mmol, 1 equiv) in DMSO (0.2 mL) at 10° C., 30% H2O2 (17 μL, 0.146 mmol, 2 equiv) was added dropwise. After stirring at room temperature the mixture for 4 h, the mixture was diluted with DMSO and filtered. The filtrate was submitted for preparative HPLC purification: HPLC system (XBridge™ Prep C18, 5 μm, 19×100 mm column); 8 min LC; flow: 20 mL/min; gradient: from 30% to 70% acetonitrile in water 0.1% TFA; isolating the final product (25 mg, 81% yield).

Workup

  1. filtrationfiltered
  2. customThe filtrate was submitted for preparative HPLC purification
  3. custom8 min LC

Sources & evidence

ORD record
ord-2f8ddc8a8f9e47e3a0384f8786265605
Source dataset
uspto-grants-2014_10
Patent number
US08853240B2

Reaction notes

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