Sodium Nitrite → 6-(1-(6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)ethyl)-5,7-difluoroquinoline

HRID 1892436Notes

Reaction equation

HRID 1892436 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]([C:11]2[C:12]([F:22])=[C:13]3[C:18](=[CH:19][C:20]=2[F:21])[N:17]=[CH:16][CH:15]=[CH:14]3)[CH3:10])[C:5]([NH2:23])=[N:4][CH:3]=1.[N:24]([O-])=O.[Na+]>C(O)(=O)C.O>[Br:1][C:2]1[N:7]=[C:6]2[N:8]([CH:9]([C:11]3[C:12]([F:22])=[C:13]4[C:18](=[CH:19][C:20]=3[F:21])[N:17]=[CH:16][CH:15]=[CH:14]4)[CH3:10])[N:24]=[N:23][C:5]2=[N:4][CH:3]=1

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 581905596-Bromo-N2-(1-(5,7-difluoroquinolin-6-yl)ethyl)pyrazine-2,3-diamine

Product 1

HCID 581904656-(1-(6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)ethyl)-5,7-difluoroquinolineYield 91%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 6-bromo-N2-(1-(5,7-difluoroquinolin-6-yl)ethyl)pyrazine-2,3-diamine (450 mg, 1.2 mmol) in acetic acid (12 mL) was added a solution of sodium nitrite (82.0 mg, 1.2 mmol) in water (2 mL). After stirring at rt for 2 hours, the solvent was removed in vacuo. The residue was diluted with NaHCO3 (aq.), extracted with DCM. The organic layer was separated and washed with water, dried over Na2SO4, filtered and concentrated in vacuo to give the title compound as a yellow solid (423 mg, 91%). 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.01 (dd, 1H), 8.95 (s, 1H), 8.52 (d, 1H), 7.75 (d, 1H), 7.64 (dd, 1H), 6.77 (q, 1H), 2.30 (d, 3H). LCMS (method A): [MH]+=391/393, tR=5.59 min.

Workup

  1. customthe solvent was removed in vacuo
  2. additionThe residue was diluted with NaHCO3 (aq.)
  3. extractionextracted with DCM
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-86850279e6a54a66b387ec5d0a676c9c
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

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