Triethylamine → 2-[(E)-1-[3-[(6-fluoro-1-methylindazol-5-yl)methyl]imidazo[1,2-b]pyridazin-6-yl]ethylideneamino]oxyethanol

HRID 1959715노트

반응식

HRID 1959715 반응식
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH3:11])=[CH:4][C:3]=1[CH2:12][C:13]1[N:17]2[N:18]=[C:19]([C:22](=O)[CH3:23])[CH:20]=[CH:21][C:16]2=[N:15][CH:14]=1.Cl.[NH2:26][O:27][CH2:28][CH2:29][OH:30].C(N(CC)CC)C>CO>[OH:30][CH2:29][CH2:28][O:27]/[N:26]=[C:22](/[C:19]1[CH:20]=[CH:21][C:16]2[N:17]([C:13]([CH2:12][C:3]3[CH:4]=[C:5]4[C:9](=[CH:10][C:2]=3[F:1])[N:8]([CH3:11])[N:7]=[CH:6]4)=[CH:14][N:15]=2)[N:18]=1)\[CH3:23]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 22507086Ethanol, 2-(aminooxy)-, hydrochlorideHCID 581905131-(3-((6-Fluoro-1-methyl-1H-indazol-5-yl)methyl)imidazo[1,2-b]pyridazin-6-yl)ethanone

생성물 1

HCID 581905452-[(E)-1-[3-[(6-fluoro-1-methylindazol-5-yl)methyl]imidazo[1,2-b]pyridazin-6-yl]ethylideneamino]oxyethanol수율 72.5%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
30 °C

실험 절차

To a solution of 1-(3-((6-fluoro-1-methyl-1H-indazol-5-yl)methyl)imidazo[1,2-b]pyridazin-6-yl)ethanone (50 mg, 0.155 mmol) in methanol (7 mL) was added 2-(aminooxy)ethanol hydrochloride (17.6 mg, 0.155 mmol). Triethyl amine was added dropwise to adjust the pH to 5˜6. The reaction mixture was stirred at 30° C. for 20 h. The solvent was removed in vacuo and the residue was dissolved in DCM, washed with NaHCO3 (aq) and brine. The organic layer was dried over Na2SO4 and concentrated in vacuo to afford the crude product which was purified by column chromatography to afford 43 mg (70%) of the title compound. 1H-NMR (400 MHz, DMSO-d6) δ ppm 8.05 (d, 1H), 7.97 (s, 1H), 7.70 (d, 1H), 7.63 (d, 1H), 7.62 (s, 1H), 7.53 (d, 1H), 4.75 (t, 1H), 4.43 (s, 1H), 4.23 (t, 2H), 3.97 (s, 3H), 3.68 (q, 2H), 2.28 (s, 3H). LCMS (method B): [MH]+=383, tR=2.45 min.

후처리

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in DCM
  3. washwashed with NaHCO3 (aq) and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto afford the crude product which
  7. customwas purified by column chromatography

출처 및 근거

ORD 기록
ord-c04bdabb6dd74e5fab8950793c89def9
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410264B2

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