Potassium Carbonate → N-Ethyl-N'-[5-(1,3-oxazol-5-yl)-7-pyridin-3-yl[1,2,4]triazolo[1,5-a]pyridin-2-yl]urea

HRID 2112944Notes

Reaction equation

HRID 2112944 reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[N:23]=[C:10]2[CH:11]=[C:12]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:13]=[C:14]([CH:15]=[O:16])[N:9]2[N:8]=1)=[O:5])[CH3:2].S([CH2:34][N+:35]#[C-:36])(C1C=CC(C)=CC=1)(=O)=O.C([O-])([O-])=O.[K+].[K+]>CO>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[N:23]=[C:10]2[CH:11]=[C:12]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:13]=[C:14]([C:15]3[O:16][CH:36]=[N:35][CH:34]=3)[N:9]2[N:8]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 866180221-Ethyl-3-(5-formyl-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-urea

Product 1

HCID 68837050N-Ethyl-N'-[5-(1,3-oxazol-5-yl)-7-pyridin-3-yl[1,2,4]triazolo[1,5-a]pyridin-2-yl]urea

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of the product of Step 2 (40 mg, 0.13 mmol), tosylmethyl isocyanide (28 mg, 0.14 mmol) and K2CO3 (36 mg, 0.26 mmol) were stirred at room temperature in MeOH (5 mL) for a few minutes, then heated at reflux for 0.5 h. All solvent was then removed under reduced pressure, the residue taken up into MeOH/CH2Cl2, and dried onto silica. Purification was carried out by filtration through a plug of silica gel (5% MeOH/CH2Cl2 as eluant) to give the title compound as a solid. LCMS (APCI+) 350.

Workup

  1. temperatureheated
  2. temperatureat reflux for 0.5 h
  3. customAll solvent was then removed under reduced pressure
  4. customdried onto silica
  5. customPurification
  6. filtrationwas carried out by filtration through a plug of silica gel (5% MeOH/CH2Cl2 as eluant)

Sources & evidence

ORD record
ord-1da3b33fccf747dfa1e08c46994f9879
Source dataset
uspto-grants-2009_04
Patent number
US07524860B2

Reaction notes

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