Triethylamine → N-cyclopropyl-4-methyl-3-(2-(6-(2-morpholinoethylamino)pyridin-3-yl)ethynyl)benzamide

HRID 1042637Notizen

Reaktionsgleichung

[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[N:7][CH:8]=1)#[CH:2].[CH:18]1([NH:21][C:22](=[O:31])[C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[C:25](I)[CH:24]=2)[CH2:20][CH2:19]1.C(N(CC)CC)C>O1CCOCC1.CCOC(C)=O.[Cu]I>[CH:18]1([NH:21][C:22](=[O:31])[C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[C:25]([C:2]#[C:1][C:3]3[CH:8]=[N:7][C:6]([NH:9][CH2:10][CH2:11][N:12]4[CH2:13][CH2:14][O:15][CH2:16][CH2:17]4)=[CH:5][CH:4]=3)[CH:24]=2)[CH2:19][CH2:20]1

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

5-Ethynyl-N-(2-morpholinoethyl)pyridin-2-amine (0.54 g, 2.36 mmol), N-cyclopropyl-3-iodo-4-methylbenzamide (0.71 g, 2.36 mmol), and triethylamine (0.49 mL, 3.54 mmol) were dissolved in dioxane (10 mL) before these were sparged with nitrogen for 15 min.; palladium dichloro-bis-triphenylphosphine (83 mg, 0.12 mmol) and copper (I) iodide (45 mg, 0.24 mmol) were added before the reaction mixture was heated to 90° C. for 6 h. The reaction mixture was diluted with 100 mL EtOAc, washed with 50 mL saturated, aqueous NaHCO3, and dried over anhydrous Na2SO4. After purification by chromatography, the title compound was obtained as a yellow oil. MS (ES+): 406 (M+H)−.

Aufarbeitung

customthese were sparged with nitrogen for 15 min.
washwashed with 50 mL saturated
dry with materialaqueous NaHCO3, and dried over anhydrous Na2SO4
customAfter purification by chromatography

Quellen und Nachweise

ORD-Eintrag: ord-4560e2f82b3845d4b4c2d2407a6313d3
Quelldatensatz: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08557996B2

Notizen zur Reaktion

Wird geladen…