Water → 2-Butyl-5-((2,6-dimethyl-4-phenylpyridin-3-yl)methylamino)isoindolin-1-one

HRID 1182706

반응식

HRID 1182706 반응식
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:5]2.C([O-])([O-])=O.[K+].[K+].CS(O[CH2:27][C:28]1[C:29]([CH3:41])=[N:30][C:31]([CH3:40])=[CH:32][C:33]=1[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)(=O)=O.O>CN(C=O)C>[CH2:12]([N:6]1[CH2:5][C:4]2[C:8](=[CH:9][CH:10]=[C:2]([NH:1][CH2:27][C:28]3[C:29]([CH3:41])=[N:30][C:31]([CH3:40])=[CH:32][C:33]=3[C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH:3]=2)[C:7]1=[O:11])[CH2:13][CH2:14][CH3:15]

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 674320655-Amino-2-butyl-2,3-dihydro-1H-isoindol-1-oneHCID 86658032(2,6-Dimethyl-4-phenylpyridin-3-yl)methyl methanesulfonate

생성물 1

HCID 674343322-Butyl-5-((2,6-dimethyl-4-phenylpyridin-3-yl)methylamino)isoindolin-1-one수율 41.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

5-Amino-2-butylisoindolin-1-one (63.1 mg, 0.309 mmol), K2CO3 (85 mg, 0.618 mmol) and KI (51.3 mg, 0.309 mmol) were added to a solution of (2,6-dimethyl-4-phenylpyridin-3-yl)methyl methanesulfonate (90 mg, 0.309 mmol) in DMF (6 mL). After stirring overnight, water was added, the mixture was extracted with EtOAc, the combined organic layers were washed with water and dried (MgSO4). Purification by flash chromatography (DCM/MeOH, gradient 2-8% MeOH) provided 2-butyl-5-((2,6-dimethyl-4-phenylpyridin-3-yl)methylamino)isoindolin-1-one (51 mg, 40%).

후처리

  1. extractionthe mixture was extracted with EtOAc
  2. washthe combined organic layers were washed with water
  3. dry with materialdried (MgSO4)
  4. customPurification by flash chromatography (DCM/MeOH, gradient 2-8% MeOH)

출처 및 근거

ORD 기록
ord-ba1400901ce04b89b7aa7b68a227d483
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08664214B2

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