Nitrogen → HCID 90019740, Verbindung

HRID 2175059Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2175059
N#N.Cl[C:4]1[N:9]=[C:8]([NH:10][C@H:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([F:20])[CH:18]=3)[CH2:13][CH2:12]2)[C:7]([N+:21]([O-:23])=[O:22])=[CH:6][CH:5]=1.[CH3:24][C:25]1[NH:29][N:28]=[C:27]([NH2:30])[CH:26]=1.C(N(C(C)C)CC)(C)C>CO.O.CS(C)=O>[F:20][C:17]1[CH:18]=[C:19]2[C:14]([CH2:13][CH2:12][C@H:11]2[NH:10][C:8]2[C:7]([N+:21]([O-:23])=[O:22])=[CH:6][CH:5]=[C:4]([NH:30][C:27]3[CH:26]=[C:25]([CH3:24])[NH:29][N:28]=3)[N:9]=2)=[CH:15][CH:16]=1

Komponenten

8

Edukt 4

HCID 947NitrogenHCID 81531DiisopropylethylamineHCID 931461H-Pyrazol-3-amine, 5-methyl-HCID 90019210HCID 90019210, Verbindung

Produkt 1

HCID 90019740HCID 90019740, VerbindungAusbeute 90,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Equip a 3 neck flask (22 L) with a thermocouple, condenser, overhead stirrer, N2 inlet, and heating mantle. To the flask, charge 6-chloro-N-[(1R)-6-fluoro-2,3-dihydro-1H-inden-1-yl]-3-nitropyridin-2-amine (600 g, 1.95 mol), 5-methyl-1H-pyrazol-3-amine (208.31 g, 2.14 mol), dimethylsulfoxide (6.0 L), and diisopropylethylamine (680.11 mL, 3.90 moles). Stir the solution at 70° C. for 20 hours. Cool the mixture to ambient temperature and dilute it with MeOH (6.0 L). Add de-ionized water (2.1 L) to the solution over one hour to give in an orange suspension. Stir the suspension for one hour, and then filter through polypropylene. Wash the filter cake with de-ionized water (12 L), transfer the solid to a tared dish and vacuum-dry (50° C.) to constant weight to provide the title compound (647 g, 90%). MS (m/z): 369 (M+1).

Aufarbeitung

  1. temperatureheating mantle
  2. temperatureCool the mixture to ambient temperature
  3. customto give in an orange suspension
  4. stirringStir the suspension for one hour
  5. filtrationfilter through polypropylene
  6. washWash the filter cake with de-ionized water (12 L)
  7. customvacuum-dry (50° C.) to constant weight

Quellen und Nachweise

ORD-Eintrag
ord-cc7e99e91f3e4db893a4a6336e9fae8b
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09062050B2

Notizen zur Reaktion

Wird geladen…