Water → 1-{2-[4-(9H-imidazo[1',2':1,2]imidazo[4,5-b]pyridin-9-yl)phenoxy]-1H-benzimidazol-1-yl}-2-methylpropan-2-ol

HRID 572182ノート

反応式

HRID 572182 の反応式
C[Mg]Br.[CH2:4]1COCC1.[N:9]1[CH:10]=[CH:11][N:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[N:14]([C:21]3[CH:40]=[CH:39][C:24]([O:25][C:26]4[N:30]([CH2:31][C:32](=[O:34])[CH3:33])[C:29]5[CH:35]=[CH:36][CH:37]=[CH:38][C:28]=5[N:27]=4)=[CH:23][CH:22]=3)[C:13]=12.O>C1COCC1>[N:9]1[CH:10]=[CH:11][N:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[N:14]([C:21]3[CH:22]=[CH:23][C:24]([O:25][C:26]4[N:30]([CH2:31][C:32]([CH3:4])([OH:34])[CH3:33])[C:29]5[CH:35]=[CH:36][CH:37]=[CH:38][C:28]=5[N:27]=4)=[CH:39][CH:40]=3)[C:13]=12

参加物

5

反応物 3

HCID 962WaterHCID 867049891-{2-[4-(9H-imidazo[1',2':1,2]imidazo[4,5-b]pyridin-9-yl)phenoxy]-1H-benzimidazol-1-yl}propan-2-oneHCID 178420675HCID 178420675、化合物

生成物 1

HCID 683505881-{2-[4-(9H-imidazo[1',2':1,2]imidazo[4,5-b]pyridin-9-yl)phenoxy]-1H-benzimidazol-1-yl}-2-methylpropan-2-ol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a suspension of cerium chloride(III) (296 mg) in THF (4 ml) was added dropwise 1 M methylmagnesium bromide-THF solution (1.2 ml) at −78° C. After stirring for 10 min, a solution of 1-{2-[4-(9H-imidazo[1′,2′:1,2]imidazo[4,5-b]pyridin-9-yl)phenoxy]-1H-benzimidazol-1-yl}propan-2-one (338 mg) obtained in Example 10 in THF (20 ml) was added dropwise at −78° C., and the obtained mixture was warmed to room temperature. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was subjected to basic silica gel column chromatography (hexane/ethyl acetate), purified by HPLC (L-Column 2 ODS, 10 mM aqueous hydrogen carbonate ammonium-containing acetonitrile solution) and recrystallized from methanol/water to give the title compound (44.0 mg).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. custompurified by HPLC (L-Column 2 ODS, 10 mM aqueous hydrogen carbonate ammonium-containing acetonitrile solution)
  6. customrecrystallized from methanol/water

出典と根拠

ORDレコード
ord-989d4094304248b5a670ebde80fa6552
出典データセット
uspto-grants-2015_05
特許番号
US09029388B2

反応ノート

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