1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Tert-butyl 4-(2-(7-bromoquinoxalin-2-yl)hydrazinecarbonyl)piperidine-1-carboxylate

HRID 711379

Reaktionsgleichung

Reaktionsgleichung von HRID 711379
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8]([NH:12][NH2:13])=[N:9]2)=[CH:4][CH:3]=1.[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH:24]([C:27](O)=[O:28])[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8]([NH:12][NH:13][C:27]([CH:24]3[CH2:25][CH2:26][N:21]([C:19]([O:18][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:20])[CH2:22][CH2:23]3)=[O:28])=[N:9]2)=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 52002657-Bromo-2-hydrazinylquinoxaline

Produkt 1

HCID 66803410Tert-butyl 4-(2-(7-bromoquinoxalin-2-yl)hydrazinecarbonyl)piperidine-1-carboxylateAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 7-bromo-2-hydrazinylquinoxaline (3 g, 12.55 mmol), 1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (3.16 g, 13.81 mmol), EDCI (2.89 g, 15.06 mmol), HOBt (2.03 g, 15.06 mmol), and TEA (1.9 g, 18.83 mmol) in DMF (100 mL) was stirred at r.t. overnight. The mixture was diluted with water (10 mL), and extracted with EtOAc (3×100 mL). The combined layers were dried over Na2SO4, and concentrated in vacuo to afford tert-butyl 4-(2-(7-bromoquinoxalin-2-yl)hydrazinecarbonyl)piperidine-1-carboxylate as pale yellow solid (3.5 g, yield 62%).

Aufarbeitung

  1. extractionextracted with EtOAc (3×100 mL)
  2. dry with materialThe combined layers were dried over Na2SO4
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6daeb1f3657544e390363fbe587464e1
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181264B2

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