Pyrrolidine → HCID 44540960, Verbindung

HRID 1616018Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1616018
Cl[C:2]1[N:7]=[C:6]([C:8]([NH:10][C:11]2[CH:19]=[C:18]([C:20]3[CH:28]=[CH:27][CH:26]=[C:25]4[C:21]=3[CH:22]=[CH:23][NH:24]4)[CH:17]=[C:16]3[C:12]=2[CH:13]=[N:14][NH:15]3)=[O:9])[CH:5]=[CH:4][CH:3]=1.[NH:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1.CCN(C(C)C)C(C)C>CS(C)=O.CS(C)=O.CO>[NH:24]1[C:25]2[C:21](=[C:20]([C:18]3[CH:17]=[C:16]4[C:12]([CH:13]=[N:14][NH:15]4)=[C:11]([NH:10][C:8]([C:6]4[CH:5]=[CH:4][CH:3]=[C:2]([N:29]5[CH2:33][CH2:32][CH2:31][CH2:30]5)[N:7]=4)=[O:9])[CH:19]=3)[CH:28]=[CH:27][CH:26]=2)[CH:22]=[CH:23]1

Komponenten

6

Edukt 3

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 44540963HCID 44540963, Verbindung

Produkt 1

HCID 44540960HCID 44540960, VerbindungAusbeute 16 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 22036561Dimethyl sulfoxide methanolLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

To a microwave vial was added 2 ml of a solution of 6-chloro-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-2-pyridinecarboxamide (350 mg, 0.26 mmol, prepared as described in Example 18) in DMSO (14 ml). Pyrrolidine (0.022 ml, 0.26 mmol) and DIPEA (0.113 ml) were added and the mixture was heated at 160° C. for 3 h under microwave irradiation. The crude reaction mixture was dissolved in DMSO/MeOH (1:1) and purified by Mass Directed Automated Preparative HPLC (Method B). Product-containing fractions were dried under a stream of nitrogen to afford the title compound (17.6 mg).

Aufarbeitung

  1. customThe crude reaction mixture
  2. custompurified by Mass Directed Automated Preparative HPLC (Method B)
  3. customProduct-containing fractions were dried under a stream of nitrogen

Quellen und Nachweise

ORD-Eintrag
ord-0309e3c32948481aa75e2cac999a2b6a
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765743B2

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