Ethylamine → HCID 44541048, Verbindung

HRID 1616014Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1616014
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.[CH2:29]([NH2:31])[CH3:30].CCN(C(C)C)C(C)C>CS(C)=O.CS(C)=O.CO>[CH2:29]([NH:31][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)[CH3:30]

Komponenten

6

Edukt 3

HCID 6341Ethylamine5×HCID 81531Diisopropylethylamine3×HCID 44540963HCID 44540963, Verbindung

Produkt 1

HCID 44541048HCID 44541048, VerbindungAusbeute 3,2 %

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, 0.90 mmol, prepared as described in Example 18) in DMSO (14 ml). Ethylamine (0.021 ml, 0.26 mmol) and DIPEA (0.113 ml) were added and the mixture was heated at 160° C. for 2 h under microwave irradiation. Further ethylamine (0.021 ml, 0.26 mmol) was added and the mixture was heated at 160° C. for 2 h under microwave irradiation. Again, ethylamine (0.021 ml, 0.26 mmol) was added and the mixture was heated at 160° C. for 1 h under microwave irradiation. After this time ethylamine (0.021 ml, 0.26 mmol) and DIPEA (0.113 ml) were both added to the mixture and it was heated at 160° C. for 2 h under microwave irradiation. Finally, additional ethylamine (0.021 ml, 0.26 mmol) and DIPEA (0.113 ml) were added and the mixture was heated at 170° C. for 1 h under microwave irradiation. The crude reaction mixture was dissolved in DMSO/MeOH (1:1) and purified by Mass Directed Automated Preparative HPLC (Method E). The sample was re-purified by Mass Directed Automated Preparative HPLC (Method E, using Waters Atlantis column 100 mm×19 mm, 5 um). Product-containing fractions were dried under a stream of nitrogen to afford the title compound (3.3 mg).

Aufarbeitung

  1. temperaturethe mixture was heated at 160° C. for 2 h under microwave irradiation
  2. temperaturethe mixture was heated at 160° C. for 1 h under microwave irradiation
  3. additionboth added to the mixture and it
  4. temperaturewas heated at 160° C. for 2 h under microwave irradiation
  5. temperaturethe mixture was heated at 170° C. for 1 h under microwave irradiation
  6. customThe crude reaction mixture
  7. custompurified by Mass Directed Automated Preparative HPLC (Method E)
  8. customThe sample was re-purified by Mass Directed Automated Preparative HPLC (Method E, using Waters Atlantis column 100 mm×19 mm, 5 um)
  9. customProduct-containing fractions were dried under a stream of nitrogen

Quellen und Nachweise

ORD-Eintrag
ord-7958c17424ac4c3aaf167016e588e3d7
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765743B2

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