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Dimethyl Sulfoxide → HCID 178516972, Verbindung

HRID 707449
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 707449
Cl.[NH2:2][C@H:3]1[CH2:6][C@H:5]([N:7]2[C:11]3=[N:12][CH:13]=[C:14]([Br:16])[N:15]=[C:10]3[N:9]([CH:17]3[CH2:19][CH2:18]3)[C:8]2=[O:20])[CH2:4]1.Cl[C:22]1[N:31]=[CH:30][C:29]2[C:24](=[CH:25][C:26]([F:32])=[CH:27][CH:28]=2)[N:23]=1.CS(C)=O.C(N(CC)C(C)C)(C)C>O.Cl.O1CCOCC1>[Br:16][C:14]1[N:15]=[C:10]2[N:9]([CH:17]3[CH2:18][CH2:19]3)[C:8](=[O:20])[N:7]([C@H:5]3[CH2:6][C@H:3]([NH:2][C:22]4[N:31]=[CH:30][C:29]5[C:24](=[CH:25][C:26]([F:32])=[CH:27][CH:28]=5)[N:23]=4)[CH2:4]3)[C:11]2=[N:12][CH:13]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 210739782-Chloro-7-fluoroquinazolineHCID 178479283HCID 178479283, Verbindung2×

Produkt 1

HCID 178516972HCID 178516972, VerbindungAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313
Hydrochloric Acid
Lösungsmittel
HCID 962WaterLösungsmittel
HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A glass microwave reaction vessel was charged with 1-(trans-3-aminocyclobutyl)-5-bromo-3-cyclopropyl-1H-imidazo[4,5-b]pyrazin-2(3H)-one hydrochloride (Intermediate 82, 0.143 g, 0.397 mmol) and 2-chloro-7-fluoroquinazoline (0.118 g, 0.646 mmol). DMSO (2 mL) was added followed by N,N-diisopropylethylamine (0.300 mL, 1.725 mmol) and the reaction mixture was sealed under argon and heated at 100° C. overnight. The reaction was cooled room temperature and diluted with water. The precipitate was filtered to give an off-white solid. The material was dissolved in 4M HCl in dioxane and purified by reverse-phase HPLC (Gilson; Gemini-NX 10 m C18 110A AXIA, 100×50 mm column) eluting with 0.1% TFA-H2O:0.1% TFA CH3CN (9:1→1:9). The fractions containing the desired product were combined and concentrated in vacuo. The residue was dissolved in MeOH and loaded onto an Si-Carbonate (Silicycle) cartridge eluting with DCM/MeOH to give 50 mg (27%) of a white crystalline solid. ESI MS 469.9, 471.8 [M+1].

Aufarbeitung

  1. customA glass microwave reaction vessel
  2. customthe reaction mixture was sealed under argon
  3. temperatureThe reaction was cooled room temperature
  4. filtrationThe precipitate was filtered
  5. customto give an off-white solid
  6. custompurified by reverse-phase HPLC (Gilson; Gemini-NX 10 m C18 110A AXIA, 100×50 mm column)
  7. washeluting with 0.1% TFA-H2O
  8. additionThe fractions containing the desired product
  9. concentrationconcentrated in vacuo
  10. dissolutionThe residue was dissolved in MeOH
  11. washeluting with DCM/MeOH

Quellen und Nachweise

ORD-Eintrag
ord-72129a68a69f4e57ba81603c9736c3b3
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09174992B2

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