Sodium Bicarbonate → 5-((4-(Benzylamino)pyridin-3-yl)methylamino)-2-butylisoindolin-1-one

HRID 1182708Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1182708
[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.[CH2:16]([NH:23][C:24]1[C:29]([CH:30]=O)=[CH:28][N:27]=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C([O-])(O)=O.[Na+]>C(O)(=O)C.O>[CH2:16]([NH:23][C:24]1[CH:25]=[CH:26][N:27]=[CH:28][C:29]=1[CH2:30][NH: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:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

8

Edukt 5

HCID 516892Sodium BicarbonateHCID 2724942TriacetoxyborohydrideHCID 5049666Sodium triacetoxyborohydrideHCID 674320655-Amino-2-butyl-2,3-dihydro-1H-isoindol-1-oneHCID 866580334-(Benzylamino)nicotinaldehyde

Produkt 1

HCID 674340235-((4-(Benzylamino)pyridin-3-yl)methylamino)-2-butylisoindolin-1-oneAusbeute 16,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

5-Amino-2-butylisoindolin-1-one (48.1 mg, 0.236 mmol) was added to a solution of 4-(benzylamino)nicotinaldehyde (50 mg, 0.236 mmol) in acetic acid (0.5 mL). Sodium triacetoxyborohydride (100 mg, 0.471 mmol) was added and the reaction mixture was stirred for 2 days. After the addition of more triacetoxyborohydride (50 mg, 0.235 mmol) and stirring for 6 h, water and sat aqueous NaHCO3 solution were added. The mixture was extracted with EtOAc, the combined org. layers washed with water and dried (MgSO4). Purification by HPLC provided 5-((4-(benzylamino)pyridin-3-yl)methylamino)-2-butylisoindolin-1-one (16 mg, 13%). ESI-MS [M+H+]=401.2.

Aufarbeitung

  1. stirringstirring for 6 h
  2. additionwere added
  3. extractionThe mixture was extracted with EtOAc
  4. washlayers washed with water
  5. dry with materialdried (MgSO4)
  6. customPurification by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-b00caaae28b74d5cb153bb5063aaecb1
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08664214B2

Notizen zur Reaktion

Wird geladen…