2-Pyrazinecarboxylic acid → HCID 12628624, compound

HRID 1270136Notes

Reaction equation

HRID 1270136 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.C(N(CC)CC)C.[N-:17]=[N+:18]=[N-:19]>C1COCC1>[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]([N:17]=[N+:18]=[N-:19])=[O:9]

Participants

5

Reactant 3

HCID 10472-Pyrazinecarboxylic acidHCID 8471TriethylamineHCID 33558Azide

Product 1

HCID 12628624HCID 12628624, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of Pyrazine-2-carboxylic acid (295 mg, 2.1 mmol, 1 eq) and triethylamine (765 ul, 5.4 mmol, 2.6 eq) in THF (6 ml) at 0° C. was added dropwise diphenylphophoryl azide (1.4 ml, 2.8 mmol, 1.3 eq). The mixture was stirred under nitrogen at 0° C. for 30 minutes, then warmed to RT and stirring continued for a further 2 hours. The reaction mixture was concentrated under vacuum and purified by flash chromatography (90/10-60/40 Iso-hexane/EtOAc) to afford the title compound as white solid (265 mg, yield=78%). 1H NMR (400 MHz, CDCl3) δ 9.14 (d, 1H, J=1.2); 8.50 (dt, 1H, J=1.2, 0.4), 2.62 (s, 3H, broad).

Workup

  1. temperaturewarmed to RT
  2. stirringstirring
  3. waitcontinued for a further 2 hours
  4. concentrationThe reaction mixture was concentrated under vacuum
  5. custompurified by flash chromatography (90/10-60/40 Iso-hexane/EtOAc)

Sources & evidence

ORD record
ord-258472f8815845e78e429fecfbd154f4
Source dataset
uspto-grants-2007_04
Patent number
US07202244B2

Reaction notes

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