Hydrochloric Acid → 1-[3-(7-Fluoro-quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl]-ethanone
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][C:25]=3[F:26])[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>[F:26][C:25]1[CH:24]=[C:23]2[C:18]([CH:19]=[CH:20][CH:21]=[N:22]2)=[CH:17][C:16]=1[CH2:15][N:12]1[C:10]2[C:9](=[N:8][CH:7]=[C:6]([C:4](=[O:3])[CH3:5])[N:11]=2)[N:14]=[N:13]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 6-[6-(1-ethoxy-vinyl)-[1,2,3]triazolo[4,5-b]pyrazin-1-ylmethyl]-7-fluoro-quinoline (600.0 mg, 0.89 mmol) and 3 N HCl (0.1 mL) in acetic acid was stirred at 50° C. for 2 h. The solvent was removed under reduced pressure. The residue was diluted with water; the pH of solution was adjusted to around 8 with aqueous NaHCO3; extracted with DCM twice. The combined organic layers were washed sequentially with water and brine, dried over Na2SO4, filtered and concentrated in vacuo to give the title compound as white solid (630 mg, 96%). 1H-NMR (400 MHz, CDCl3) δ ppm 9.46 (s, 1H), 8.94 (d, 1H), 8.11 (d, 2H), 7.85 (dd, 1H), 7.41 (dd, 1H), 6.23 (s, 2H), 2.79 (s, 3H). LCMS (method A): [MH]+=323, tR=2.23 min.
Workup
- customThe solvent was removed under reduced pressure
- additionThe residue was diluted with water
- extractionextracted with DCM twice
- washThe combined organic layers were washed sequentially with water and brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-117b81cdfbbc4f9db235e6030dfa161a
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08410264B2
Reaction notes
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