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

HRID 1182707

Reaction equation

HRID 1182707 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-dafe9df8dd884e4aae5de41dfe250f89
Source dataset
uspto-grants-2014_03
Patent number
US08664214B2

Linked notes

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