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

HRID 1182707

Reaktionsgleichung

Reaktionsgleichung von HRID 1182707
[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]

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-dafe9df8dd884e4aae5de41dfe250f89
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08664214B2

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