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

HRID 456122Notes

Reaction equation

HRID 456122 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 the 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 in vacuo. The residue was taken with NaHCO3(aq), extracted with DCM. The organic layer was washed with NH4Cl(aq), dried over Na2SO4, filtered, concentrated in vacuo and purified by silica gel chromatography with EA:Hexanes to provide 6-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline (3.35 g, 47%). 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.05 (s, 1H), 8.89 (d, 1H), 8.34 (d, 1H), 8.02 (d, 1H), 7.9 3 (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 in vacuo
  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 silica gel chromatography with EA

Sources & evidence

ORD record
ord-f840a073099346b0b09316e594df46e7
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Reaction notes

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