tert-Butyl 4-(5-bromo-3-((1-(hydroxyamino)ethylidene)amino)pyrazin-2-yl)piperazine-1-carboxylate → 5-Bromo-2-methyl-8-(piperazin-1-yl)-[1,2,4]triazolo[1,5-a]pyrazine

HRID 1045748Notes

Reaction equation

HRID 1045748 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([N:21]=[C:22]([NH:24]O)[CH3:23])[C:5]([N:8]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)=[N:6][CH:7]=1>C([O-])(O)=O.[Na+]>[Br:1][C:2]1[N:3]2[N:24]=[C:22]([CH3:23])[N:21]=[C:4]2[C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1

Participants

3

Reactant 1

HCID 136056833tert-Butyl 4-(5-bromo-3-((1-(hydroxyamino)ethylidene)amino)pyrazin-2-yl)piperazine-1-carboxylate

Product 1

HCID 584470575-Bromo-2-methyl-8-(piperazin-1-yl)-[1,2,4]triazolo[1,5-a]pyrazineYield 61.2%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

In a 50 mL round bottom flask, tert-butyl 4-(5-bromo-3-((1-(hydroxyamino)ethylidene)amino)pyrazin-2-yl)piperazine-1-carboxylate (2.3 g, 5.5 mmol) was treated with polyphosphoric acid (10 g) at 50° C. for 1 h then at 75° C. for 1.75 h. Work-up: the mixture was carefully neutralized with saturated aqueous NaHCO3 (300 mL) and extracted with CH2Cl2 (100 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with 5% EtOAc in CH2Cl2 (containing 2% Et3N), to afford 1.0 g (61%) of the product as a white solid. MS m/z: 297 (M+H+).

Workup

  1. extractionextracted with CH2Cl2 (100 mL×3)
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash column chromatography on silica gel with 5% EtOAc in CH2Cl2 (containing 2% Et3N)

Sources & evidence

ORD record
ord-8c0015ddd64748fdb520119d501dc537
Source dataset
uspto-grants-2013_10
Patent number
US08569300B2

Reaction notes

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