Ethanol, 2-(aminooxy)-, hydrochloride → 2-[(E)-1-[3-[(5,7-difluoroquinolin-6-yl)methyl]triazolo[4,5-b]pyrazin-5-yl]ethylideneamino]oxyethanol

HRID 1959763노트

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HRID 1959763 반응식
[F:1][C:2]1[C:11]([CH2:12][N:13]2[C:17]3=[N:18][C:19]([C:22](=O)[CH3:23])=[CH:20][N:21]=[C:16]3[N:15]=[N:14]2)=[C:10]([F:25])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.Cl.[NH2:27][O:28][CH2:29][CH2:30][OH:31]>CO>[OH:31][CH2:30][CH2:29][O:28]/[N:27]=[C:22](/[C:19]1[N:18]=[C:17]2[N:13]([CH2:12][C:11]3[C:2]([F:1])=[C:3]4[C:8](=[CH:9][C:10]=3[F:25])[N:7]=[CH:6][CH:5]=[CH:4]4)[N:14]=[N:15][C:16]2=[N:21][CH:20]=1)\[CH3:23]

참가 물질

4

반응물 2

HCID 22507086Ethanol, 2-(aminooxy)-, hydrochloride2회HCID 698122851-(1-((5,7-difluoroquinolin-6-yl)methyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone

생성물 1

HCID 880045562-[(E)-1-[3-[(5,7-difluoroquinolin-6-yl)methyl]triazolo[4,5-b]pyrazin-5-yl]ethylideneamino]oxyethanol수율 60.1%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
50 °C

실험 절차

To a solution of 1-(1-((5,7-difluoroquinolin-6-yl)methyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone (3.5 mg, 0.01 mmol) in MeOH (1 mL), 2-(aminooxy)ethanol hydrochloride (intermediate S) (1.6 mg, 0.02 mmol) was added, the solution was heated to 50° C. for overnight. The solvent was removed in vacuo. The residue was diluted with water, treated with aqueous NaHCO3 solution, extracted with DCM. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by prepared HPLC to give white solid (E)-1-(1-((5,7-difluoroquinolin-6-yl)methyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone O-2-hydroxyethyl oxime (2.4 mg, 56%). 1H-NMR (400 MHz, CDCl3) δ ppm 9.38 (s, 1H), 8.98 (d, 1H), 8.42 (d, 1H), 7.64 (d, 1H), 7.48 (m, 1H), 6.18 (s, 2H), 4.45 (m, 2H), 3.98 (m, 2H), 2.36 (s, 3H), 1.96 (m, 1H). LCMS (method B): [MH]+=399.9, tR=2.19 min.

후처리

  1. customThe solvent was removed in vacuo
  2. additionThe residue was diluted with water
  3. additiontreated with aqueous NaHCO3 solution
  4. extractionextracted with DCM
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified
  9. customby prepared HPLC

출처 및 근거

ORD 기록
ord-4dbac5db42e248c2a6df52d2a976dcd9
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410264B2

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