N-bromobutanimide → HCID 57917273、化合物

HRID 69293ノート

反応式

HRID 69293 の反応式
[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

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 442062913-Imidazo[1,2-a]pyridin-6-ylmethyl-6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazine

生成物 1

HCID 57917273HCID 57917273、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4d15d5f155504882ab957d587dcffb01
出典データセット
uspto-grants-2014_09
特許番号
US08822468B2

反応ノート

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