Ethyl isocyanate → 1-Ethyl-3-[7-(6-methoxy-pyridin-3-yl)-5-(2-methyl-oxazol-5-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-urea

HRID 2112982Notes

Reaction equation

HRID 2112982 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:14]=[C:13]([C:15]3[O:19][C:18]([CH3:20])=[N:17][CH:16]=3)[N:12]3[N:21]=[C:22]([NH2:24])[N:23]=[C:11]3[CH:10]=2)=[CH:5][CH:4]=1.[CH2:25]([N:27]=[C:28]=[O:29])[CH3:26].[Sn](OC(C)=O)(OC(C)=O)(CCCC)CCCC.CO.C(Cl)(Cl)Cl>O1CCOCC1.CO.C(Cl)Cl>[CH2:25]([NH:27][C:28]([NH:24][C:22]1[N:23]=[C:11]2[CH:10]=[C:9]([C:6]3[CH:7]=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH:14]=[C:13]([C:15]3[O:19][C:18]([CH3:20])=[N:17][CH:16]=3)[N:12]2[N:21]=1)=[O:29])[CH3:26]

Participants

7

Reactant 4

HCID 8022Ethyl isocyanateHCID 16682740Dibutyltin diacetateHCID 21584188Chloroform methanolHCID 688359877-(6-Methoxy-pyridin-3-yl)-5-(2-methyl-oxazol-5-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine

Product 1

HCID 688389581-Ethyl-3-[7-(6-methoxy-pyridin-3-yl)-5-(2-methyl-oxazol-5-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-urea

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A mixture of the product of Step 1 (0.14 g, 0.43 mmol), EtNCO (0.15 g, 2.2 mmol) and SnBu2(OAc)2 in dioxane (4 mL) was microwaved at 125° C. for 1 h. The resulting solid was collected by filtration and recrystallized from DMF to give the target compound. Pre-adsorption of a MeOH/CHCl3 solution of this compound onto SiO2 and column chromatography (5% MeOH/DCM) gave the title compound as a solid. MS m/z 394 (M+H+).

Workup

  1. customwas microwaved at 125° C. for 1 h
  2. filtrationThe resulting solid was collected by filtration
  3. customrecrystallized from DMF
  4. customto give the target compound

Sources & evidence

ORD record
ord-4a23703f888e4fd28292e9b95f91ff5c
Source dataset
uspto-grants-2009_04
Patent number
US07524860B2

Reaction notes

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