N-溴代丁二酰亚胺(NBS) → HCID 57917273，化合物

HRID 69293笔记

反应方程式

HRID 69293 反应方程式
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[C:8]([CH2:10][C:11]3[N:15]4[N:16]=[C:17]([C:20]5[CH:21]=[N:22][N:23]([CH3:25])[CH:24]=5)[CH:18]=[CH:19][C:14]4=[N:13][CH:12]=3)[CH:7]=[CH:6][C:5]=12.C1C(=O)N([Br:33])C(=O)C1>C(Cl)Cl>[Br:33][C:3]1[N:4]2[CH:9]=[C:8]([CH2:10][C:11]3[N:15]4[N:16]=[C:17]([C:20]5[CH:21]=[N:22][N:23]([CH3:25])[CH:24]=5)[CH:18]=[CH:19][C:14]4=[N:13][CH:12]=3)[CH:7]=[CH:6][C:5]2=[N:1][CH:2]=1

参与物

4

反应物 2

HCID 67184N-溴代丁二酰亚胺(NBS)HCID 442062913-Imidazo[1,2-a]pyridin-6-ylmethyl-6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazine

产物 1

HCID 57917273HCID 57917273，化合物

试剂、催化剂与溶剂 1

HCID 6344二氯甲烷溶剂

实验过程

3-Imidazo[1,2-a]pyridin-6-ylmethyl-6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazine (Example 10, 10 mg, 0.030 mmol) was dissolved in DCM (0.3 mL) with NBS (5.9 mg, 0.033 mmol). The RM was stirred at rt for 2 h. The solvent was removed. The residue was purified by preparative HPLC with acetonitrile and water (+0.1% TFA). The fractions were joined and the acetonitrile was removed. The aqueous solution was basified with 5% NaHCO3 solution and it was extracted with EtOAc/MeOH (9:1) twice. Combined organic layers was washed with brine and dried over Na2SO4, filtered and concentrated. The solid obtained was triturated with Et2O. The precipitate was filtered off to afford the title compound as a white solid (tR 0.7 min (conditions 2), MH+=408).

后处理

  1. customThe solvent was removed
  2. customThe residue was purified by preparative HPLC with acetonitrile and water (+0.1% TFA)
  3. customthe acetonitrile was removed
  4. extractionwas extracted with EtOAc/MeOH (9:1) twice
  5. washCombined organic layers was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe solid obtained
  10. customwas triturated with Et2O
  11. filtrationThe precipitate was filtered off

来源与证据

ORD记录
ord-4d15d5f155504882ab957d587dcffb01
来源数据集
uspto-grants-2014_09
专利号
US08822468B2

反应笔记

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