Water → 2-butyl-5-((4-(trifluoromethyl)pyridin-3-yl)methylamino)isoindolin-1-one TFA

HRID 1182707ノート

反応式

HRID 1182707 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.[F:16][C:17]([F:27])([F:26])[C:18]1[C:23]([CH:24]=O)=[CH:22][N:21]=[CH:20][CH:19]=1.[OH2:28]>CO.[Cl-].[Cl-].[Zn+2]>[OH:28][C:18]([C:17]([F:27])([F:26])[F:16])=[O:11].[CH2:12]([N:6]1[CH2:5][C:4]2[C:8](=[CH:9][CH:10]=[C:2]([NH:1][CH2:24][C:23]3[CH:22]=[N:21][CH:20]=[CH:19][C:18]=3[C:17]([F:27])([F:16])[F:26])[CH:3]=2)[C:7]1=[O:11])[CH2:13][CH2:14][CH3:15]

参加物

6

反応物 3

HCID 962WaterHCID 213547244-(Trifluoromethyl)pyridine-3-carbaldehydeHCID 674320655-Amino-2-butyl-2,3-dihydro-1H-isoindol-1-one

生成物 1

HCID 867622862-butyl-5-((4-(trifluoromethyl)pyridin-3-yl)methylamino)isoindolin-1-one TFA収率 19%

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 887Methanol溶媒

実験手順

5-amino-2-butylisoindolin-1-one (35.0 mg, 0.17 mmol), ZnCl2 (14.0 mg, 0.10 mmol) and NaCNBH4 (12.9 mg, 0.21 mmol) were consecutively added to a solution of 4-(trifluoromethyl)nicotinaldehyde (30.0 mg, 0.17 mmol) in MeOH (4 mL). After stirring overnight at room temperature excess water was added. The reaction mixture was extracted with EtOAc, the combined org. layers were washed with water, dried (MgSO4) and the solvent was removed in vacuo. Purification by HPLC provided 2-butyl-5-((4-(trifluoromethyl)pyridin-3-yl)methylamino)isoindolin-1-one TFA (16.0 mg, 19%). ESI-MS [M+H]+=364.2.

後処理

  1. additionwas added
  2. extractionThe reaction mixture was extracted with EtOAc
  3. washlayers were washed with water
  4. dry with materialdried (MgSO4)
  5. customthe solvent was removed in vacuo
  6. customPurification by HPLC

出典と根拠

ORDレコード
ord-dafe9df8dd884e4aae5de41dfe250f89
出典データセット
uspto-grants-2014_03
特許番号
US08664214B2

反応ノート

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