Acetic Acid → 6-[1,2,3]Triazolo[4,5-b]pyrazin-1-ylmethyl-quinoline

HRID 15996

Reaction equation

HRID 15996 reaction equation
Br[C:2]1[N:7]=[C:6]2[N:8]([CH2:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][CH:16]=[CH:15]4)[N:9]=[N:10][C:5]2=[N:4][CH:3]=1.CC(O)=O.CCOC(C)=O.[H][H]>CO.[Pd]>[N:8]1([CH2:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]=[CH:17][CH:16]=[CH:15]3)[C:6]2=[N:7][CH:2]=[CH:3][N:4]=[C:5]2[N:10]=[N:9]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 547756086-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 593419336-[1,2,3]Triazolo[4,5-b]pyrazin-1-ylmethyl-quinolineYield 20%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

A solution of 6-(6-bromo-[1,2,3]triazolo[4,5-b]pyrazin-1-ylmethyl)-quinoline (200 mg, 0.586 mmol) in MeOH (10 mL):AcOH (1 mL): EtOAc (1 mL) was degassed 3 times with nitrogen. To this solution was added Pd/C (20 mg). A balloon containing hydrogen was added via syringe and the reaction was allowed to stir for 18 hours at room temperature. The reaction did not complete and more Pd/C was added (20 mg) and stirred for 18 hours at room temperature. The reaction was stopped when LCMS showed a ratio of 1:1 (product:starting material). The reaction was filtered over celite and washed with EtOAc (50 mL). The filtered solution was concentrated and purified by Biotage silica gel column chromatography with EtOAc: Hexanes to give 30 mg of the product 6-[1,2,3]triazolo[4,5-b]pyrazin-1-ylmethyl-quinoline (20% yield).

Workup

  1. additionwas added via syringe
  2. stirringstirred for 18 hours at room temperature
  3. filtrationThe reaction was filtered over celite
  4. washwashed with EtOAc (50 mL)
  5. concentrationThe filtered solution was concentrated
  6. custompurified by Biotage silica gel column chromatography with EtOAc

Sources & evidence

ORD record
ord-4825ae5a95894914b5d5be85049a19ca
Source dataset
uspto-grants-2010_06
Patent number
US07732604B2

Linked notes

Loading…