Cyclopropylamine → HCID 44540959, Verbindung

HRID 1616016Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1616016
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.[CH:29]1([NH2:32])[CH2:31][CH2:30]1.CCN(C(C)C)C(C)C>CS(C)=O.CS(C)=O.CO>[CH:29]1([NH:32][C:2]2[N:7]=[C:6]([C:8]([NH:10][C:11]3[CH:19]=[C:18]([C:20]4[CH:28]=[CH:27][CH:26]=[C:25]5[C:21]=4[CH:22]=[CH:23][NH:24]5)[CH:17]=[C:16]4[C:12]=3[CH:13]=[N:14][NH:15]4)=[O:9])[CH:5]=[CH:4][CH:3]=2)[CH2:31][CH2:30]1

Komponenten

6

Edukt 3

HCID 69828Cyclopropylamine4×HCID 81531Diisopropylethylamine2×HCID 44540963HCID 44540963, Verbindung

Produkt 1

HCID 44540959HCID 44540959, VerbindungAusbeute 1,8 %

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). Cyclopropylamine (0.018 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 cyclopropylamine (0.018 ml, 0.26 mmol) was added and the mixture was heated at 160° C. for 2 h under microwave irradiation. Again, cyclopropylamine (0.018 ml, 0.26 mmol) was added and the mixture was heated at 160° C. for 1 h under microwave irradiation. After this time, cyclopropylamine (0.018 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. 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 (1.9 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. customThe crude reaction mixture
  6. custompurified by Mass Directed Automated Preparative HPLC (Method E)
  7. customThe sample was re-purified by Mass Directed Automated Preparative HPLC (Method E, using Waters Atlantis column 100 mm×19 mm, 5 um)
  8. customProduct-containing fractions were dried under a stream of nitrogen

Quellen und Nachweise

ORD-Eintrag
ord-fe33e8b639e947729a0171e8ab668df8
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765743B2

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