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Hydrochloric Acid → 1-[3-(7-Fluoro-quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl]-ethanone

HRID 456167
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Reaktionsgleichung

Reaktionsgleichung von HRID 456167
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]1
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Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 581904906-[6-(1-Ethoxy-vinyl)-[1,2,3]triazolo[4,5-b]pyrazin-1-ylmethyl]-7-fluoro-quinoline

Produkt 1

HCID 581905781-[3-(7-Fluoro-quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl]-ethanoneAusbeute 219,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A solution of the 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 hour. The solvent was removed under reduced pressure. The residue was diluted with water, adjusted the pH value of solution 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 a white solid (630 mg, 96%). 1H1H-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.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. additionThe residue was diluted with water
  3. extractionextracted with DCM twice
  4. washThe combined organic layers were washed sequentially with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4530b042ed724b88a6504b2cfed4c8aa
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08497368B2

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