Ethanol, 2-(aminooxy)-, hydrochloride → 1-[3-(7-Fluoro-quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl]-ethanone O-(2-hydroxy-ethyl)-oxime

HRID 1892339노트

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HRID 1892339 반응식
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[CH2:12][N:13]1[C:21]2[C:16](=[N:17][CH:18]=[C:19]([C:22](=O)[CH3:23])[N:20]=2)[N:15]=[N:14]1.Cl.[NH2:26][O:27][CH2:28][CH2:29][OH:30]>CO>[OH:30][CH2:29][CH2:28][O:27][N:26]=[C:22]([C:19]1[N:20]=[C:21]2[N:13]([CH2:12][C:3]3[CH:4]=[C:5]4[C:10](=[CH:11][C:2]=3[F:1])[N:9]=[CH:8][CH:7]=[CH:6]4)[N:14]=[N:15][C:16]2=[N:17][CH:18]=1)[CH3:23]

참가 물질

4

반응물 2

HCID 22507086Ethanol, 2-(aminooxy)-, hydrochlorideHCID 581905781-[3-(7-Fluoro-quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl]-ethanone

생성물 1

HCID 767200901-[3-(7-Fluoro-quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl]-ethanone O-(2-hydroxy-ethyl)-oxime수율 74.7%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
45 °C

실험 절차

To a solution of 1-[3-(7-fluoro-quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl]-ethanone (190.0 mg, 0.59 mmol) in MeOH (40 mL) was added 2-(aminooxy)ethanol hydrochloride (134.0 mg, 1.18 mol). The mixture was heated at 45° C. overnight. The solvent was removed under reduced pressure. The residue was purified by column chromatography with gradient (DCM:MeOH=10:1) to give the title compound as a white solid (168.0 mg, 71%). 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.30 (s, 1H), 8.93 (d, 1H), 8.41 (d, 1H), 8.19 (d, 1H), 7.83 (d, 1H), 7.54 (dd, 1H), 6.24 (s, 2H), 4.78 (t, 1H), 4.31 (t, 2H), 3.72 (m, 2H), 2.29 (s, 3H). LCMS (method A): [MH]+=382, tR=4.99 min.

후처리

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was purified by column chromatography with gradient (DCM:MeOH=10:1)

출처 및 근거

ORD 기록
ord-1d81fa3e0f6049798da9975081bfd9b5
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507676B2

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