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3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline → 2-(2-(1,3-Dimethyl-1H-pyrazol-5-yl)-8-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)acetonitrile

HRID 252
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 252
COc1cc(N)ccc1-n1cnc(C)c1.Cc1cc(C2CN(CC#N)Cc3ccc(Cl)nc3O2)n(C)n1>CC(=O)O.CC(=O)O.COCCOC.O=C([O-])[O-].[Cs+].[Cs+].[Pd].c1ccc(-c2ccccc2P(C2CCCCC2)C2CCCCC2)cc1>COc1cc(Nc2ccc3c(n2)OC(c2cc(C)nn2C)CN(CC#N)C3)ccc1-n1cnc(C)c1
KomponentenReaktionsbedingungenVersuchsvorschriftQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 2

HCID 454801813-methoxy-4-(4-methyl-1H-imidazol-1-yl)anilineHCID 595778162-(8-chloro-2-(1,3-dimethyl-1H-pyrazol-5-yl)-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)acetonitrile

Produkt 1

HCID 498189412-(2-(1,3-Dimethyl-1H-pyrazol-5-yl)-8-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)acetonitrileAusbeute 16,55 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 10796
Cesium carbonate
Reagenz
HCID 27342162-(Dicyclohexylphosphino)biphenylKatalysator
HCID 4144353Palladium (II) acetateKatalysator
HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (0.068 g, 0.34 mmol),2-(8-chloro-2-(1,3-dimethyl-1H-pyrazol-5-yl)-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)acetonitrile (0.107 g, 0.34 mmol) Palladium acetate (7.56 mg, 0.03 mmol) and Cesium carbonate (0.329 g, 1.01 mmol) were added in a microwave vial. The mixture was capped and flushed with argon.1,2-dimethoxyethane (5 mL) was added, the reaction mixture was flushed with argon and the mixture was run in a microwave for 60 minutes at 100°C. Reaction complete. The reaction mixture was filtrated through Celite and washed with dichloromethane. The filtrate was concentrated and the crude product was purified by preparative chromatography. The productcontaining fractions were pooled, concentrated and the residue was partitioned between sat. NaHCO3 (aq) and dichloromethane. The organic layer was separated by a Phase Separator and concentrated giving 2-(2-(1,3-dimethyl-1H-pyrazol-5-yl)-8-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)acetonitrile (0.027 g, 16.55 %).

Quellen und Nachweise

ORD-Eintrag
ord-0ff30e2abe284325a98db1564fc934f7
Quelldatensatz
750 AstraZeneca ELN dataset
Originallink
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