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

HRID 1182707

반응식

HRID 1182707 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.[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-dafe9df8dd884e4aae5de41dfe250f89
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08664214B2

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