N-methyl-5-(5-methylhexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-2-nitrobenzamide → 2-amino-N-methyl-5-(5-methylhexahydropyrrolo[3,4-c]pyrrole-2(1H)-yl)benzamide

HRID 77375

Reaktionsgleichung

Reaktionsgleichung von HRID 77375
[CH3:1][NH:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:17][CH:16]3[CH:12]([CH2:13][N:14]([CH3:18])[CH2:15]3)[CH2:11]2)[CH:7]=[CH:6][C:5]=1[N+:19]([O-])=O.[H][H]>C(O)C.[Pd]>[NH2:19][C:5]1[CH:6]=[CH:7][C:8]([N:10]2[CH2:11][CH:12]3[CH:16]([CH2:15][N:14]([CH3:18])[CH2:13]3)[CH2:17]2)=[CH:9][C:4]=1[C:3]([NH:2][CH3:1])=[O:22]

Komponenten

5

Edukt 2

HCID 69929569N-methyl-5-(5-methylhexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-2-nitrobenzamide2×HCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 699285982-amino-N-methyl-5-(5-methylhexahydropyrrolo[3,4-c]pyrrole-2(1H)-yl)benzamideAusbeute 101,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

N-methyl-5-(5-methylhexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-2-nitrobenzamide (Intermediate 13A) (900 mg, 2.96 mmol) was dissolved in ethanol (140 mL). The resulting solution was hydrogenated using the H-cube at 40° C. under 30 bar pressure of hydrogen, with a flow rate of 1 mL per minute through a 10% palladium on charcoal cartridge. The reaction mixture was concentrated to afford 2-amino-N-methyl-5-(5-methylhexahydropyrrolo[3,4-c]pyrrole-2(1H)-yl)benzamide, (824 mg, 3.01 mmol).

Aufarbeitung

  1. customat 40° C.
  2. concentrationThe reaction mixture was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-716e1d925f254b47bfec5c934480b5dd
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841289B2

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