Ethyl isocyanate → HCID 66628276, Verbindung

HRID 2200980Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2200980
[NH2:1][C:2]1[N:31]=[C:5]2[N:6]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)[C:7]([CH3:20])=[C:8]([C:18]#[N:19])[C@@H:9]([C:10]3[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=3)[N:4]2[N:3]=1.S([O-])([O-])(=O)=O.[Na+].[Na+].[CH2:39]([N:41]=[C:42]=[O:43])[CH3:40]>N1C=CC=CC=1>[C:18]([C:8]1[C@@H:9]([C:10]2[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=2)[N:4]2[N:3]=[C:2]([NH:1][C:42]([NH:41][CH2:39][CH3:40])=[O:43])[N:31]=[C:5]2[N:6]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:28])([F:30])[F:29])[CH:22]=2)[C:7]=1[CH3:20])#[N:19]

Komponenten

5

Edukt 3

HCID 8022Ethyl isocyanateHCID 24436Sodium SulfateHCID 66627900HCID 66627900, Verbindung

Produkt 1

HCID 66628276HCID 66628276, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Under an atmosphere of argon protective gas, (7R)-2-amino-7-(4-cyanophenyl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitrile (15 mg, 33 μmol) was dissolved in abs. pyridine (2 ml), and solid sodium sulfate (spatula tip) and ethyl isocyanate (46.6 mg, 655 μmol, 20 eq.) were added. The reaction mixture was then heated in a microwave reactor (2.5 h at 100° C., then 2 h at 110° C. and finally 2 h at 125° C.). After cooling, the reaction mixture was filtered, the filtrate was concentrated under reduced pressure and the residue was purified by preparative HPLC (Gromsil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA). After lyophilization, the product was obtained as a solid (7.8 mg, 48% of theory).

Aufarbeitung

  1. custom2 h
  2. customat 110° C.
  3. customfinally 2 h
  4. customat 125° C.
  5. temperatureAfter cooling
  6. filtrationthe reaction mixture was filtered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customthe residue was purified by preparative HPLC (Gromsil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA)
  9. customAfter lyophilization, the product was obtained as a solid (7.8 mg, 48% of theory)

Quellen und Nachweise

ORD-Eintrag
ord-051700be43bf41c3ad5d8417636cebe4
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09359362B2

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