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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 1892338
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HRID 1892338 반응식
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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참가 물질

4

반응물 2

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

생성물 1

HCID 581905781-[3-(7-Fluoro-quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl]-ethanone수율 219.6%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7e4387fd0e53461e8f468d56c6f083ef
출처 데이터셋
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08507676B2

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