2-(3-Ethyl-ureido)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid methoxy-methyl-amide → 1-(5-Butyryl-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-3-ethyl-urea

HRID 2112955Notes

Reaction equation

HRID 2112955 reaction equation
[CH2:1]([Mg]Cl)[CH2:2][CH3:3].CON(C)[C:9]([C:11]1[N:16]2[N:17]=[C:18]([NH:20][C:21]([NH:23][CH2:24][CH3:25])=[O:22])[N:19]=[C:15]2[CH:14]=[C:13]([C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[CH:12]=1)=[O:10]>O1CCCC1.[NH4+].[Cl-]>[C:9]([C:11]1[N:16]2[N:17]=[C:18]([NH:20][C:21]([NH:23][CH2:24][CH3:25])=[O:22])[N:19]=[C:15]2[CH:14]=[C:13]([C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[CH:12]=1)(=[O:10])[CH2:1][CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 866180232-(3-Ethyl-ureido)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid methoxy-methyl-amideHCID 178455855HCID 178455855, compound

Product 1

HCID 688353671-(5-Butyryl-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-3-ethyl-urea

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 25517Ammonium ChlorideSolvent

Procedure

Propylmagnesium chloride (1.00 mL) was cooled to 0° C. then charged with 2-(3-ethyl-ureido)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid methoxy-methyl-amide (252 mg, 0.682 mmol) in tetrahydrofuran (4.00 mL). After 24 h the reaction was diluted with tetrahydrofuran and neutralized with NH4Cl. The organic was dried over magnesium sulfate and concentrated leaving a solid. The crude was recrystallized (ethyl acetate) to afford the final product 1-(5-butyryl-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-2-yl)-3-ethyl-urea. MS (APCI+): m/z 353.4 (M+H).

Workup

  1. dry with materialThe organic was dried over magnesium sulfate
  2. concentrationconcentrated
  3. customleaving a solid
  4. customThe crude was recrystallized (ethyl acetate)

Sources & evidence

ORD record
ord-b09e0b64b74345f091d77f30f0f3ce0e
Source dataset
uspto-grants-2009_04
Patent number
US07524860B2

Reaction notes

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