Ethanolamine → N-cyclopropyl-4-[4-(2-hydroxy-ethylamino)-imidazo[1,2-a]quinoxalin-1-yl]-benzamide

HRID 1025485Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1025485
Br[C:2]1[N:6]2[C:7]3[C:12]([N:13]=[C:14](Cl)[C:5]2=[N:4][CH:3]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.[NH2:16][CH2:17][CH2:18][OH:19].CCN(C(C)C)C(C)C.[CH:29]1([NH:32][C:33]([C:35]2[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=2)=[O:34])[CH2:31][CH2:30]1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(=O)([O-])[O-].[K+].[K+]>[CH:29]1([NH:32][C:33](=[O:34])[C:35]2[CH:40]=[CH:39][C:38]([C:2]3[N:6]4[C:7]5[C:12]([N:13]=[C:14]([NH:16][CH2:17][CH2:18][OH:19])[C:5]4=[N:4][CH:3]=3)=[CH:11][CH:10]=[CH:9][CH:8]=5)=[CH:37][CH:36]=2)[CH2:30][CH2:31]1

Komponenten

7

Edukt 4

HCID 700EthanolamineHCID 81531DiisopropylethylamineHCID 2773359(4-(Cyclopropylcarbamoyl)phenyl)boronic acidHCID 717416391-Bromo-4-chloroimidazo[1,2-A]quinoxaline

Produkt 1

HCID 49802724N-cyclopropyl-4-[4-(2-hydroxy-ethylamino)-imidazo[1,2-a]quinoxalin-1-yl]-benzamideAusbeute 13 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 11430Potassium CarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

(1-bromo-4-chloro-imidazo[1,2-a]quinoxaline (intermediate example 1.1, 1 mL, 0.2M in NMP), 2-amino-ethanol (2 eq, 0.8 mL, 0.5 M in NMP) and DIPEA (3 eq, 103 μL) were combined in a sealed vial and heated at 170° C. under microwave irradiation for 60 min. After cooling, [4-[(cyclopropylamino)carbonyl]phenyl]-boronic acid (1.5 eq, 0.3 mL, 1 M in NMP), Pd(dppf)Cl2 (0.1 eq, 533 μL, 0.0375 M in NMP) and potassium carbonate (600 μL, 1M in water) were added and the mixture was heated at 140° C. under microwave irradiation for 40 min. After cooling, the solution was filtered and subjected to preparative HPLC to give N-cyclopropyl-4-[4-(2-hydroxy-ethylamino)-imidazo[1,2-a]quinoxalin-1-yl]-benzamide (10.19 mg, 13%): UPLC-MS: RT==0.82 min; m/z (ES+) 388.4 [MH+]; required MW=387.4.

Aufarbeitung

  1. temperatureAfter cooling
  2. temperaturethe mixture was heated at 140° C. under microwave irradiation for 40 min
  3. temperatureAfter cooling
  4. filtrationthe solution was filtered

Quellen und Nachweise

ORD-Eintrag
ord-6fb52968d7484460890fb5f7b2b3155c
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08729082B2

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