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

HRID 456124

반응식

HRID 456124 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][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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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 the solution was stirred at rt for 2 h, solvents was removed under reduced pressure. The residue was diluted with water and its pH was adjusted to basic with aqueous NaHCO3, 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 silica gel column chromatography to give a yellow solid of 1-(1-(quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone (131 mg, 91%). 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.

후처리

  1. customsolvents 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 silica gel column chromatography

출처 및 근거

ORD 기록
ord-b86a5ba8604544a4a2fd897bc14af30c
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497368B2

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