HCID 66599464, Verbindung → HCID 66605740, Verbindung

HRID 2410855Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2410855
C([N:8]1[C:16]2[CH:15]=[C:14]([O:17][CH3:18])[CH:13]=[CH:12][C:11]=2[C:10]2[N:19]=[C:20]([N:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)[CH:21]=[C:22]([C:23]([O:25][CH3:26])=[O:24])[C:9]1=2)C1C=CC=CC=1>C(O)(C(F)(F)F)=O.FC(F)(F)S(O)(=O)=O>[CH3:18][O:17][C:14]1[CH:13]=[CH:12][C:11]2[C:10]3[N:19]=[C:20]([N:27]4[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]4)[CH:21]=[C:22]([C:23]([O:25][CH3:26])=[O:24])[C:9]=3[NH:8][C:16]=2[CH:15]=1

Komponenten

4

Edukt 1

HCID 66599464HCID 66599464, Verbindung

Produkt 1

HCID 66605740HCID 66605740, VerbindungAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 62406Trifluoromethanesulfonic acidKatalysator2×HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

A solution of methyl 5-benzyl-7-methoxy-2-(piperidin-1-yl)-5H-pyrido[3,2-b]indole-4-carboxylate (51 mg, 0.12 mmol) in TFA (2 mL) and two drops of trifluoromethanesulfonic acid was heated at reflux for 30 min. Another two drops of trifluoromethanesulfonic acid was added and heating continued for another 40 min. Preparative HPLC (100×30 mm Luna C18 column, Solvent A=10 mM NH4OAc in 95% water:5% acetonitrile; B=10 mM NH4OAc in 5% water:95% acetonitrile; gradient of 15 to 100% B over 20 min at 42 mL/min) followed by removal of the solvents afforded methyl 7-methoxy-2-(piperidin-1-yl)-5H-pyrido[3,2-b]indole-4-carboxylate (15 mg, 0.044 mmol, 37% yield). MS (ESI) m/z 340.2 (M+H). 1H NMR (500 MHz, chloroform-d) δ ppm 9.02 (1H, br. s.), 8.09 (1H, d, J=8.85 Hz), 7.22 (1H, s), 6.89 (1H, s), 6.85 (1H, d, J=8.55 Hz), 4.02 (3H, s), 3.90 (3H, s), 3.53-3.64 (4H, m), 1.69-1.80 (4H, m), 1.56-1.67 (2H, m).

Aufarbeitung

  1. temperatureat reflux for 30 min
  2. temperatureheating
  3. customPreparative HPLC (100×30 mm Luna C18 column, Solvent A=10 mM NH4OAc in 95% water:5% acetonitrile; B=10 mM NH4OAc in 5% water:95% acetonitrile; gradient of 15 to 100% B over 20 min at 42 mL/min) followed by removal of the solvents

Quellen und Nachweise

ORD-Eintrag
ord-8b4b0be6ba77434192cf682a6c96572a
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08815840B2

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