Acetone → 4-[4-(2,5,7-Trimethyl-3H-imidazo[4,5-b]pyridin-3-ylmethyl)phenylamino]methyl-1-(1-methylethyl)piperidine

HRID 1890655ノート

反応式

HRID 1890655 の反応式
[CH3:1][C:2]1[N:12]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][CH2:21][CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)=[CH:16][CH:15]=2)[C:5]2=[N:6][C:7]([CH3:11])=[CH:8][C:9]([CH3:10])=[C:4]2[N:3]=1.[CH3:28][C:29]([CH3:31])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCCl>[CH3:1][C:2]1[N:12]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][CH2:21][CH:22]3[CH2:23][CH2:24][N:25]([CH:29]([CH3:31])[CH3:28])[CH2:26][CH2:27]3)=[CH:16][CH:15]=2)[C:5]2=[N:6][C:7]([CH3:11])=[CH:8][C:9]([CH3:10])=[C:4]2[N:3]=1

参加物

6

反応物 4

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 23156137HCID 23156137、化合物

生成物 1

HCID 231561364-[4-(2,5,7-Trimethyl-3H-imidazo[4,5-b]pyridin-3-ylmethyl)phenylamino]methyl-1-(1-methylethyl)piperidine収率 52.6%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

A solution of Compound 157 (0.350 g, 0.97 mmol) in 1,2-dichloroethane was added with acetone (0.106 mL, 1.46 mmol) followed by stirring for 20 minutes. The mixture was added with sodium triacetoxyborohydride (0.616 g, 2.91 mmol) followed by stirring at room temperature overnight. The reaction mixture was added with a 2 mol/L aqueous sodium hydroxide solution and extracted with dichloromethane three times. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:2 mol/L ammonia-methanol solution=19:1). The obtained crystals were recrystallized from ethanol-diisopropyl ether to obtain Compound 161 (0.205 g, 0.51 mmol, 52%).

後処理

  1. stirringby stirring at room temperature overnight
  2. extractionextracted with dichloromethane three times
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform:2 mol/L ammonia-methanol solution=19:1)
  6. customThe obtained crystals were recrystallized from ethanol-diisopropyl ether

出典と根拠

ORDレコード
ord-63aa4c57ef5b47be8b9a522f41c2b653
出典データセット
uspto-grants-2013_08
特許番号
US08507484B2

反応ノート

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