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

HRID 1959763ノート

反応式

HRID 1959763 の反応式
[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]

参加物

4

反応物 2

HCID 22507086Ethanol, 2-(aminooxy)-, hydrochloride2 回HCID 698122851-(1-((5,7-difluoroquinolin-6-yl)methyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4dbac5db42e248c2a6df52d2a976dcd9
出典データセット
uspto-grants-2013_04
特許番号
US08410264B2

反応ノート

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