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

HRID 1890652노트

반응식

HRID 1890652 반응식
[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.[O:28]1[CH2:33][CH2:32][C:31](=O)[CH2:30][CH2:29]1.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:31]4[CH2:32][CH2:33][O:28][CH2:29][CH2:30]4)[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

참가 물질

6

반응물 4

HCID 14798Sodium HydroxideHCID 121599Tetrahydro-4H-pyran-4-oneHCID 5049666Sodium triacetoxyborohydrideHCID 23156137HCID 23156137, 화합물

생성물 1

HCID 694376334-[4-(2,5,7-Trimethyl-3H-imidazo[4,5-b]pyridin-3-ylmethyl)phenylamino]methyl-1-(4-tetrahydropyranyl)piperidine수율 54%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

A solution of Compound 157 (0.250 g, 0.69 mmol) in 1,2-dichloroethane was added with tetrahydro-4-pyranone (0.096 mL, 1.04 mmol) followed by stirring for 15 minutes. The mixture was added with sodium triacetoxyborohydride (0.439 g, 2.07 mmol) followed by stirring at room temperature for 5 hours. 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 158 (0.166 g, 0.37 mmol, 54%).

후처리

  1. stirringby stirring at room temperature for 5 hours
  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

출처 및 근거

ORD 기록
ord-7efd229823eb42b2886d37a1e5a9dad4
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507484B2

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