Sodium Nitrite → 6-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline

HRID 1959684Notes

Reaction equation

HRID 1959684 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][CH:14]=[CH:13]3)[C:5]([NH2:20])=[N:4][CH:3]=1.[N:21]([O-])=O.[Na+]>C(O)(=O)C.O>[Br:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:9][C:10]3[CH:11]=[C:12]4[C:17](=[CH:18][CH:19]=3)[N:16]=[CH:15][CH:14]=[CH:13]4)[N:21]=[N:20][C:5]2=[N:4][CH:3]=1

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 457894186-bromo-N2-(quinolin-6-ylmethyl)pyrazine-2,3-diamine

Product 1

HCID 547756086-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinolineYield 49.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 6-bromo-N2-(quinolin-6-ylmethyl)pyrazine-2,3-diamine (6.55 g, 19.84 mmol) in acetic acid (15 mL) was added a solution of sodium nitrite (2.74 g, 39.7 mmol) in water (3 mL). After stirring at rt for 3 h, the solution was concentrated. The residue was taken with NaHCO3 (aq) and extracted with DCM. The organic layer was washed with NH4Cl (aq), dried over Na2SO4, filtered, concentrated in vacuo and purified by column chromatography with EtOAc:hexane to provide 3.35 g (47%) of the title compound. 1H-NMR (400 MHz, DMSO-d6) ppm 9.05 (s, 1H), 8.89 (d, 1H), 8.34 (d, 1H), 8.02 (d, 1H), 7.93 (s, 1H), 7.76 (dd, 1H), 7.53 (dd, 1H), 6.19 (s, 2H). LCMS (method B): [MH]+=343, tR=2.11 min.

Workup

  1. concentrationthe solution was concentrated
  2. extractionextracted with DCM
  3. washThe organic layer was washed with NH4Cl (aq)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by column chromatography with EtOAc

Sources & evidence

ORD record
ord-772222c20f7b4bb7bd5752d512cd2305
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Reaction notes

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