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

HRID 1959667노트

반응식

HRID 1959667 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 (13.1) (500.0 mg, 1.60 mmol) and 2-Iodoxybenzoic acid (45%)(1488.0 mg, 2.39 mmol) in 10 mL acetone was heated at reflux for 3 h. Solvent was removed under reduced pressure. The residue was diluted with water; pH was adjusted to around 10 with 10% NaOH aqueous solution. 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
  2. temperatureat reflux for 3 h
  3. customSolvent was removed under reduced pressure
  4. additionThe residue was diluted with water
  5. filtrationThe precipitates were collected by filtration
  6. washwashed with water three times
  7. dissolutionThe solid was dissolved in DCM
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-4b9dbb0217314a9b9f38407e5f5d7e08
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410264B2

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