Trifluoroacetic acid → (R)-5-(2-chloro-6-fluorophenyl)-3-(6-(piperidin-3-yloxy)pyrazin-2-yl)-1H-indole bis(2,2,2-trifluoroacetate)

HRID 1529320Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1529320
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[C:18]1[N:23]=[C:22]([O:24][C@@H:25]2[CH2:30][CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26]2)[CH:21]=[N:20][CH:19]=1.[C:38]([OH:44])([C:40]([F:43])([F:42])[F:41])=[O:39]>C(Cl)Cl>[F:41][C:40]([F:43])([F:42])[C:38]([OH:44])=[O:39].[F:41][C:40]([F:43])([F:42])[C:38]([OH:44])=[O:39].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[C:18]1[CH:19]=[N:20][CH:21]=[C:22]([O:24][C@@H:25]2[CH2:30][CH2:29][CH2:28][NH:27][CH2:26]2)[N:23]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 67960707(R)-tert-butyl 3-(6-(5-(2-chloro-6-fluorophenyl)-1H-indol-3-yl)pyrazin-2-yloxy)piperidine-1-carboxylate

Produkt 1

HCID 86709771(R)-5-(2-chloro-6-fluorophenyl)-3-(6-(piperidin-3-yloxy)pyrazin-2-yl)-1H-indole bis(2,2,2-trifluoroacetate)

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (R)-tert-butyl 3-(6-(5-(2-chloro-6-fluorophenyl)-1H-indol-3-yl)pyrazin-2-yloxy)piperidine-1-carboxylate (0.077 g, 0.147 mmol) in 1.5 mL DCM was added TFA (0.170 mL, 2.208 mmol). After 30 min, the reaction was concentrated in vacuo, taken up in DMSO, and purified by RPHPLC, 10-100% ACN/H2O with 0.1% TFA; product-containing fractions were combined and concentrated in vacuo to give (R)-5-(2-chloro-6-fluorophenyl)-3-(6-(piperidin-3-yloxy)pyrazin-2-yl)-1H-indole bis(2,2,2-trifluoroacetate) as an orange solid. MS (ESI, pos. ion) m/z: 423 (M+1).

Aufarbeitung

  1. concentrationthe reaction was concentrated in vacuo
  2. custompurified by RPHPLC, 10-100% ACN/H2O with 0.1% TFA
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-cd6459ea45a54c91862ce327ef293f17
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090593B2

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