Hydrogen Peroxide → HCID 10251737, Verbindung

HRID 549275Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 549275
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([S:24][C:25]4[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=4)[CH:22]=3)[CH:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.OO.FC(F)(F)C(O)=[O:37].[OH-:41].[Na+]>C(OCC)(=O)C.O>[ClH:31].[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([S:24]([C:21]2[CH:22]=[C:23]3[C:18]([CH:17]=[CH:16][N:15]=[C:14]3[N:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[CH:19][CH:20]=2)(=[O:37])=[O:41])=[CH:26][CH:27]=1

Komponenten

7

Edukt 4

HCID 784Hydrogen PeroxideHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 67157202HCID 67157202, Verbindung

Produkt 1

HCID 10251737HCID 10251737, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of 4-[7-(p-chloro-phenylsulfanyl)-isoquinolin-1-yl]-piperazine-1-carboxylic acid tert-butyl ester (297 mg, 0.65 mmol), H2O2 (30% in water, 0.5 mL), trifluoroacetic acid (3 mL) was heated at 50° C., 2 h. The reaction was continued overnight at 35° C. A water solution of NaOH (1N) was added (pH=14), ethyl acetate was added and the organic phase was separated, dried (MgSO4), filtered. The filtrated was concentrated and the residue was purified by flash column chromatography (SiO2, dichloromethane:methanol 9.5:0.5→9.0:1.0) The free base was converted into hydrochloride by treatment with HCl in diethyl ether to obtained 70 mg of the title compound. 1H NMR (CH3OH-d4) δ 8.75-8.85 (m, 2H), 8.10-8.25 (m, 3H), 8.00-8.08 (m, 2H), 7.60-7.68 (m, 3H), 3.85-3.95 (m, 4H), 3.55-3.65 (m, 4H).

Aufarbeitung

  1. additionwas added
  2. customthe organic phase was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationThe filtrated was concentrated
  6. customthe residue was purified by flash column chromatography (SiO2, dichloromethane:methanol 9.5:0.5→9.0:1.0) The free base

Quellen und Nachweise

ORD-Eintrag
ord-8c1b1de219fb4cc597654e6cc0d1a860
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07943639B2

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