Diisopropylethylamine → HCID 178457831, Verbindung

HRID 518644

Reaktionsgleichung

Reaktionsgleichung von HRID 518644
Cl.[NH2:2][C@@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([NH:11][CH:12]([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.CCN(C(C)C)C(C)C.[Cl:24][C:25]1[CH:30]=[C:29](Cl)[C:28]([N+:32]([O-:34])=[O:33])=[CH:27][N:26]=1>C(#N)C.O>[Cl:24][C:25]1[CH:30]=[C:29]([NH:2][C@@H:3]2[CH2:4][CH2:5][C@H:6]([C:9]([NH:11][CH:12]([CH3:14])[CH3:13])=[O:10])[CH2:7][CH2:8]2)[C:28]([N+:32]([O-:34])=[O:33])=[CH:27][N:26]=1

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 122757652,4-Dichloro-5-nitropyridineHCID 178457872HCID 178457872, Verbindung

Produkt 1

HCID 178457831HCID 178457831, VerbindungAusbeute 73,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of cis-4-amino-N-isopropylcyclohexanecarboxamide hydrochloride (12.58 g, 57.0 mmol) and DIPEA (29.0 mL, 166 mmol) in ACN (104 mL) was added 2,4-dichloro-5-nitropyridine (10.00 g, 51.8 mmol). The resulting mixture was stirred at RT for 24 hours. The reaction mixture was diluted with water and washed with DCM (×2). The combined organic layers were washed with a minimal volume of brine, dried over sodium sulfate, filtered and concentrated in vacuo. After almost complete concentration of solvent, EtOAc was added, and the solid precipitate was collected yielding cis-4-(2-chloro-5-nitropyridin-4-ylamino)-N-isopropylcyclohexanecarboxamide as a yellow solid (12.97 g, 73.4% yield).

Aufarbeitung

  1. washwashed with DCM (×2)
  2. washThe combined organic layers were washed with a minimal volume of brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. concentrationAfter almost complete concentration of solvent, EtOAc
  7. additionwas added
  8. customthe solid precipitate was collected

Quellen und Nachweise

ORD-Eintrag
ord-a2f0400b1f944df0b7ffa6e47a56d027
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115127B2

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