Tetrahydrofuran → HCID 58447041, compound

HRID 1045728Notes

Reaction equation

HRID 1045728 reaction equation
[Br:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[N:6]([CH:8]=[N:9][N:10]=2)[CH:7]=1.[N:12]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C1COCC1>O>[Br:1][C:2]1[N:3]=[C:4]([N:15]2[CH2:14][CH2:13][N:12]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16]2)[C:5]2[N:6]([CH:8]=[N:9][N:10]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 143452tert-Butyl piperazine-1-carboxylateHCID 584469856-Bromo-8-chloro[1,2,4]triazolo[4,3-a]pyrazine

Product 1

HCID 58447041HCID 58447041, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 100 mL round bottom flask was charged with 6-bromo-8-chloro-[1,2,4]triazolo[4,3-a]pyrazine (1.11 g, 4.73 mmol), tert-butyl piperazine-1-carboxylate (2.64 g, 14.2 mmol) and THF (50 mL). The resulting mixture was stirred at room temperature for 0.5 h. Reaction progress was monitored by TLC (EtOAc/petroleum ether=1:2). Work-up: the reaction mixture was diluted with water and extracted with EtOAc (50 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was further purified by flash column chromatography on silica gel with 20% EtOAc in petroleum ether, to afford 1.62 g (89%) of the product as a yellow solid.

Workup

  1. customReaction progress
  2. extractionextracted with EtOAc (50 mL×3)
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was further purified by flash column chromatography on silica gel with 20% EtOAc in petroleum ether

Sources & evidence

ORD record
ord-cdb600c200644bc5ac4f4a30f414abf5
Source dataset
uspto-grants-2013_10
Patent number
US08569300B2

Reaction notes

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