N-bromobutanimide → (Rac)-3-[1-(3-bromo-imidazo[1,2-a]pyridin-6-yl)-ethyl]-6-(1-methyl-1h-pyrazol-4-yl)imidazo[1,2-b]pyridazine

HRID 69306노트

반응식

HRID 69306 반응식
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[C:8]([CH:10]([C:12]3[N:16]4[N:17]=[C:18]([C:21]5[CH:22]=[N:23][N:24]([CH3:26])[CH:25]=5)[CH:19]=[CH:20][C:15]4=[N:14][CH:13]=3)[CH3:11])[CH:7]=[CH:6][C:5]=12.C1C(=O)N([Br:34])C(=O)C1>C(Cl)Cl>[Br:34][C:3]1[N:4]2[CH:9]=[C:8]([CH:10]([C:12]3[N:16]4[N:17]=[C:18]([C:21]5[CH:22]=[N:23][N:24]([CH3:26])[CH:25]=5)[CH:19]=[CH:20][C:15]4=[N:14][CH:13]=3)[CH3:11])[CH:7]=[CH:6][C:5]2=[N:1][CH:2]=1

참가 물질

4

반응물 2

HCID 67184N-bromobutanimideHCID 57917425HCID 57917425, 화합물

생성물 1

HCID 57917281(Rac)-3-[1-(3-bromo-imidazo[1,2-a]pyridin-6-yl)-ethyl]-6-(1-methyl-1h-pyrazol-4-yl)imidazo[1,2-b]pyridazine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(rac)-3-(1-Imidazo[1,2-a]pyridin-6-yl-ethyl)-6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazine (Example 293, 607 mg, 1.768 mmol) was dissolved in DCM (18 mL) and NBS (346 mg, 1.944 mmol) was added. It was stirred at rt for 30 min then the solvent was removed. The residue was purified by flash chromatography (CombiFlash® Companion System®, with RediSep® silica gel column, 0 to 20% MeOH in DCM). Combined fractions were concentrated to give the title compound as a yellow solid (tR 0.7 min (conditions 2), MH+=422, 1H-NMR in DMSO-d6: 8.47 (s, 1H); 8.37 (s, 1H); 8.04 (m, 2H); 7.78 (s, 1H); 7.67 (s, 1H); 7.54 (d, 1H); 7.47 (d, 1H); 7.32 (d, 1H); 4.81 (q, 1H); 3.89 (s, 3H); 1.80 (d, 3H)).

후처리

  1. customthe solvent was removed
  2. customThe residue was purified by flash chromatography (CombiFlash® Companion System®, with RediSep® silica gel column, 0 to 20% MeOH in DCM)
  3. concentrationCombined fractions were concentrated

출처 및 근거

ORD 기록
ord-35572baab7de40f989c3136453622910
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822468B2

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