Ethanol, 2-(aminooxy)-, hydrochloride → 2-[(E)-1-[3-[(5,7-difluoroquinolin-6-yl)methyl]triazolo[4,5-b]pyrazin-5-yl]ethylideneamino]oxyethanol

HRID 1959763Notes

Reaction equation

HRID 1959763 reaction equation
[F:1][C:2]1[C:11]([CH2:12][N:13]2[C:17]3=[N:18][C:19]([C:22](=O)[CH3:23])=[CH:20][N:21]=[C:16]3[N:15]=[N:14]2)=[C:10]([F:25])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.Cl.[NH2:27][O:28][CH2:29][CH2:30][OH:31]>CO>[OH:31][CH2:30][CH2:29][O:28]/[N:27]=[C:22](/[C:19]1[N:18]=[C:17]2[N:13]([CH2:12][C:11]3[C:2]([F:1])=[C:3]4[C:8](=[CH:9][C:10]=3[F:25])[N:7]=[CH:6][CH:5]=[CH:4]4)[N:14]=[N:15][C:16]2=[N:21][CH:20]=1)\[CH3:23]

Participants

4

Reactant 2

HCID 22507086Ethanol, 2-(aminooxy)-, hydrochloride2×HCID 698122851-(1-((5,7-difluoroquinolin-6-yl)methyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone

Product 1

HCID 880045562-[(E)-1-[3-[(5,7-difluoroquinolin-6-yl)methyl]triazolo[4,5-b]pyrazin-5-yl]ethylideneamino]oxyethanolYield 60.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1-(1-((5,7-difluoroquinolin-6-yl)methyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone (3.5 mg, 0.01 mmol) in MeOH (1 mL), 2-(aminooxy)ethanol hydrochloride (intermediate S) (1.6 mg, 0.02 mmol) was added, the solution was heated to 50° C. for overnight. The solvent was removed in vacuo. The residue was diluted with water, treated with aqueous NaHCO3 solution, extracted with DCM. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by prepared HPLC to give white solid (E)-1-(1-((5,7-difluoroquinolin-6-yl)methyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone O-2-hydroxyethyl oxime (2.4 mg, 56%). 1H-NMR (400 MHz, CDCl3) δ ppm 9.38 (s, 1H), 8.98 (d, 1H), 8.42 (d, 1H), 7.64 (d, 1H), 7.48 (m, 1H), 6.18 (s, 2H), 4.45 (m, 2H), 3.98 (m, 2H), 2.36 (s, 3H), 1.96 (m, 1H). LCMS (method B): [MH]+=399.9, tR=2.19 min.

Workup

  1. customThe solvent was removed in vacuo
  2. additionThe residue was diluted with water
  3. additiontreated with aqueous NaHCO3 solution
  4. extractionextracted with DCM
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified
  9. customby prepared HPLC

Sources & evidence

ORD record
ord-4dbac5db42e248c2a6df52d2a976dcd9
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Reaction notes

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