Trifluoroacetic acid → HCID 89709222, Verbindung

HRID 1526180Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1526180
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[C:20]([CH2:21][CH3:22])=[N:19][C:18]([C:23](=[O:25])[NH2:24])=[C:17]([O:26][C:27]3[CH:32]=[CH:31][C:30]([C:33]4[CH2:34][CH2:35][N:36]([CH3:39])[CH2:37][CH:38]=4)=[CH:29][CH:28]=3)[N:16]=2)[CH:9]=1)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>ClCCl>[NH2:7][C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=1)[O:14][C:15]1[N:16]=[C:17]([O:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH2:34][CH2:35][N:36]([CH3:39])[CH2:37][CH:38]=3)=[CH:29][CH:28]=2)[C:18]([C:23]([NH2:24])=[O:25])=[N:19][C:20]=1[CH2:21][CH3:22]

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 117675490HCID 117675490, Verbindung

Produkt 1

HCID 89709222HCID 89709222, VerbindungAusbeute 45,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of tert-butyl[3-({5-carbamoyl-3-ethyl-6-[4-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)phenoxy]pyrazin-2-yl}oxy)phenyl]carbamate (150 mg) and dichloromethane (3 mL) was added trifluoroacetic acid (421 μL), followed by stirring at room temperature for 2 hours. The mixture was neutralized with a saturated aqueous sodium hydrogen carbonate solution, extracted with ethyl acetate, and then the organic phase was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH2 type, eluent; chloroform:methanol=1:0-95:5) to obtain 5-(3-aminophenoxy)-6-ethyl-3-[4-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)phenoxy]pyrazine-2-carboxamide (56 mg) as a colorless solid.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washthe organic phase was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (NH2 type, eluent; chloroform:methanol=1:0-95:5)

Quellen und Nachweise

ORD-Eintrag
ord-0bfb5c5742b54a13b4c7a94c21c0b305
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085540B2

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