Ammonia → HCID 178508482, Verbindung

HRID 244155Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 244155
Cl[C:2]1[C:3]2[N:4]([C:8]([C@H:12]3[CH2:17][CH2:16][C@H:15]([CH2:18][OH:19])[CH2:14][CH2:13]3)=[N:9][C:10]=2[I:11])[CH:5]=[CH:6][N:7]=1.C1COCC1.[NH3:25]>C(O)(C)C>[NH2:25][C:2]1[C:3]2[N:4]([C:8]([C@H:12]3[CH2:17][CH2:16][C@H:15]([CH2:18][OH:19])[CH2:14][CH2:13]3)=[N:9][C:10]=2[I:11])[CH:5]=[CH:6][N:7]=1

Komponenten

5

Edukt 3

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 178520933HCID 178520933, Verbindung

Produkt 1

HCID 178508482HCID 178508482, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

trans-[4-(8-chloro-1-iodoimidazo[1,5-a]pyrazin-3-yl)cyclohexyl]methanol (26.50 g, 67.66 mmol) was charged in a 400 mL steel bomb and was dissolved in 2M NH3 in isopropanol (300 mL) and anhydrous THF (10 mL). The reaction mixture was cooled to −78° C. Ammonia gas was bubbled vigorously into the solution for 8 min; then the bomb was tightly sealed and heated to 120° C. for 20 h. The crude reaction mixture was concentrated in vacuo, then the reaction residue was taken up with MeOH/CHCl3, loaded onto silica gel. The mixture was purified by a silica gel glass column chromatography [eluted with 1:1 CH2Cl2/EtOAc to 10%˜7 N NH3 in MeOH/CHCl3] to afford the desired product as a beige cream white solid; MS (ES+): m/z 373.01 (100) [MH+], 373.98 (50) [MH+2]; tR(polar-5 min/openlynx) 1.57 min.

Aufarbeitung

  1. customAmmonia gas was bubbled vigorously into the solution for 8 min
  2. customthen the bomb was tightly sealed
  3. temperatureheated to 120° C. for 20 h
  4. customThe crude reaction mixture
  5. concentrationwas concentrated in vacuo
  6. customThe mixture was purified by a silica gel glass column chromatography [eluted with 1:1 CH2Cl2/EtOAc to 10%˜7 N NH3 in MeOH/CHCl3]

Quellen und Nachweise

ORD-Eintrag
ord-2db892b369d143b8aeac3c3a2c5699d2
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653268B2

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