Hydrochloric Acid → 1-(1-(Quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone

HRID 1959686Notes

Reaction equation

HRID 1959686 reaction equation
C([O:3][C:4]([C:6]1[N:11]=[C:10]2[N:12]([CH2:15][C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[N:22]=[CH:21][CH:20]=[CH:19]4)[N:13]=[N:14][C:9]2=[N:8][CH:7]=1)=[CH2:5])C.Cl>C(O)(=O)C>[N:22]1[C:23]2[C:18](=[CH:17][C:16]([CH2:15][N:12]3[C:10]4=[N:11][C:6]([C:4](=[O:3])[CH3:5])=[CH:7][N:8]=[C:9]4[N:14]=[N:13]3)=[CH:25][CH:24]=2)[CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 248519576-[6-(1-Ethoxy-vinyl)[1,2,3]triazolo[4,5-b]pyrazin-1-ylmethyl]-quinoline

Product 1

HCID 593418021-(1-(Quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanoneYield 95.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of the 6-((6-(1-ethoxyvinyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline (150 mg, 0.451 mmol) in acetic acid was added 3N HCl (0.1 mL). After stirring at it for 2 h, solvent was removed under reduced pressure. The residue was diluted with water and its pH was adjusted to basic with aqueous NaHCO3, and extracted with DCM. The combined organic layers were washed with NaHCO3 (aq) and brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography to give 131 mg (91%) of the title compound as a yellow solid. 1H-NMR (400 MHz, CDCl3) δ ppm 9.45 (s, 1H), 8.95 (d, 1H), 8.14 (m, 2H), 7.95 (s, 1H), 7.84 (d, 1H), 7.45 (m, 1H), 6.19 (s, 2H), 2.75 (s, 3H). LCMS (method B): [MH]+=305, tR=2.95 min.

Workup

  1. customsolvent was removed under reduced pressure
  2. additionThe residue was diluted with water and its pH
  3. extractionextracted with DCM
  4. washThe combined organic layers were washed with NaHCO3 (aq) and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-fd96df585b374515bb321abb0ac069dc
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Reaction notes

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