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

HRID 1182706

反応式

HRID 1182706 の反応式
[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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-ba1400901ce04b89b7aa7b68a227d483
出典データセット
uspto-grants-2014_03
特許番号
US08664214B2

関連ノート

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