Ammonium Chloride → HCID 86708695, Verbindung

HRID 921797Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 921797
[Cl-].[NH4+].[Cl:3][C:4]1[C:11]([N+:12]([O-])=O)=[CH:10][C:7]([C:8]#[N:9])=[CH:6][C:5]=1[O:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22]2([CH3:26])[CH2:25][O:24][CH2:23]2)[CH2:18][CH2:17]1>CO.[Zn]>[NH2:12][C:11]1[CH:10]=[C:7]([CH:6]=[C:5]([O:15][CH:16]2[CH2:21][CH2:20][N:19]([C:22]3([CH3:26])[CH2:23][O:24][CH2:25]3)[CH2:18][CH2:17]2)[C:4]=1[Cl:3])[C:8]#[N:9]

Komponenten

5

Edukt 2

HCID 25517Ammonium ChlorideHCID 86708693HCID 86708693, Verbindung

Produkt 1

HCID 86708695HCID 86708695, VerbindungAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

Ammonium chloride (584 mg, 10.92 mmol) and zinc (356 mg, 5.46 mmol) were added to a solution of 4-chloro-3-((1-(3-methyloxetan-3-yl)piperidin-4-yl)oxy)-5-nitrobenzonitrile (96 mg, 0.273 mmol) in methanol (10 mL) and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was filtered through celite and the filtrate was concentrated, the crude was purified by flash chromatography on silica gel using an automated ISCO system (loaded onto a 24 g dry column, 24 g column, eluting with 0-6% 2 N ammonia in methanol/dichloromethane). 3-amino-4-chloro-5-((1-(3-methyloxetan-3-yl)piperidin-4-yl)oxy)benzonitrile (87 mg) was obtained as a foaming solid.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated
  3. customthe crude was purified by flash chromatography on silica gel using an automated ISCO system (
  4. customdry column, 24 g column
  5. washeluting with 0-6% 2 N ammonia in methanol/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-b4c93e393e604ef593837f607ac579cf
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273057B2

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