2-Iodoxybenzoic acid → (6-Chloroimidazo[1,2-b]pyridazin-3-yl)(1-methyl-1H-indazol-5-yl)methanone

HRID 456158노트

반응식

HRID 456158 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:11]([C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][CH:21]=3)[N:18]([CH3:22])[N:17]=[CH:16]4)[OH:12])=[CH:9][N:10]=2)[N:7]=1.I(C1C=CC=CC=1C(O)=O)(=O)=O>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][CH:21]=3)[N:18]([CH3:22])[N:17]=[CH:16]4)=[O:12])=[CH:9][N:10]=2)[N:7]=1

참가 물질

4

반응물 2

HCID 1087942-Iodoxybenzoic acidHCID 58190458(6-Chloroimidazo[1,2-b]pyridazin-3-yl)(1-methyl-1H-indazol-5-yl)methanol

생성물 1

HCID 58190472(6-Chloroimidazo[1,2-b]pyridazin-3-yl)(1-methyl-1H-indazol-5-yl)methanone수율 82.2%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A suspension of (6-chloroimidazo[1,2-b]pyridazin-3-yl)(1-methyl-1H-indazol-5-yl)methanol (500.0 mg, 1.60 mmol) and 2-Iodoxybenzoic acid (45% pure, 1488.0 mg, 2.39 mmol) in 10 mL acetone was heated at refluxe and stirred for 3 hours. Solvent was removed under reduced pressure. The residue was diluted with water, and the pH value of the solution adjusted to around 10 with 10% aqueous NaOH. The precipitates were collected by filtration and washed with water three times. The solid was dissolved in DCM, dried over Na2SO4, filtered and concentrated to give the title compound as a white solid (410.0 mg, 78%). 1H-NMR (400 MHz, DMSO-d6) δ ppm 8.46 (s, 1H), 8.42 (m, 1H), 8.32 (m, 1H), 8.27 (d, 1H), 7.95 (dd, 1H), 7.815 (d, 1H), 7.66 (d, 1H), 4.12 (s, 2H). LCMS (method A): [MH]+=312, tR=4.64 min.

후처리

  1. temperaturewas heated at refluxe
  2. customSolvent was removed under reduced pressure
  3. additionThe residue was diluted with water
  4. filtrationThe precipitates were collected by filtration
  5. washwashed with water three times
  6. dissolutionThe solid was dissolved in DCM
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-97cf965344844d9eae374bece554567a
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497368B2

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