Isovaleryl chloride → 2-amino-7-(2-dimethylamino-pyrimidin-5-yl)-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid N'-(3-methyl-butyryl)-hydrazide

HRID 2112952Notes

Reaction equation

HRID 2112952 reaction equation
[NH2:1][C:2]1[N:23]=[C:5]2[CH:6]=[C:7]([C:14]3[CH:15]=[N:16][C:17]([N:20]([CH3:22])[CH3:21])=[N:18][CH:19]=3)[CH:8]=[C:9]([C:10]([NH:12][NH2:13])=[O:11])[N:4]2[N:3]=1.[C:24](Cl)(=[O:29])[CH2:25][CH:26]([CH3:28])[CH3:27]>C1COCC1.O1CCOCC1>[CH3:27][CH:26]([CH3:28])[CH2:25][C:24]([NH:13][NH:12][C:10]([C:9]1[N:4]2[N:3]=[C:2]([NH2:1])[N:23]=[C:5]2[CH:6]=[C:7]([C:14]2[CH:19]=[N:18][C:17]([N:20]([CH3:21])[CH3:22])=[N:16][CH:15]=2)[CH:8]=1)=[O:11])=[O:29]

Participants

4

Reactant 2

HCID 66054Isovaleryl chlorideHCID 576431232-Amino-7-(2-dimethylamino-pyrimidin-5-yl)-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid hydrazide

Product 1

HCID 576431372-amino-7-(2-dimethylamino-pyrimidin-5-yl)-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid N'-(3-methyl-butyryl)-hydrazide

Reagents, catalysts & solvents 1

HCID 22018518Dioxane tetrahydrofuranSolvent

Procedure

The product of Step 2 (0.11 g, 0.35 mmol) was combined with isovaleryl chloride (0.04 mL, 0.35 mmol) and 5 mL of a 1:1 solution of THF/dioxane in a tube. The mixture was microwaved at 130° C. for five minutes. The reaction mixture was cooled, then the solid was collected by filtration to give 2-amino-7-(2-dimethylamino-pyrimidin-5-yl)-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid N′-(3-methyl-butyryl)-hydrazide. MS (APCI+): m/z 398.1.

Workup

  1. customThe mixture was microwaved at 130° C. for five minutes
  2. temperatureThe reaction mixture was cooled
  3. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-1ec50e7674314d2a8fd8bf87eb0904c5
Source dataset
uspto-grants-2009_04
Patent number
US07524860B2

Reaction notes

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