4-Chloro-3-(methanesulfonylmethyl)aniline → 5-[4-Chloro-3-(methylsulfonylmethyl)anilino]-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile

HRID 670

Reaktionsgleichung

Reaktionsgleichung von HRID 670
CS(=O)(=O)Cc1cc(N)ccc1Cl.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>CC(=O)N(C)C.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd].[Pd]>CS(=O)(=O)Cc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)ccc1Cl

Komponenten

7

Edukt 2

HCID 545940214-Chloro-3-(methanesulfonylmethyl)anilineHCID 898271735-Chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile

Produkt 1

HCID 1322560905-[4-Chloro-3-(methylsulfonylmethyl)anilino]-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrileAusbeute 35,03 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 10796Cesium carbonateReagenzHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)KatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

In a 40mL vial (t=g) was 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (88 mg, 0.38 mmol), [Reactants], and cesium carbonate (135 mg, 0.41 mmol) in DMA (0.5 mL) ([VOLUME]),Pd2(dba)3 (17.24 mg, 0.02 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (21.79 mg, 0.04 mmol) were added. to give a brown suspension. The vial was filled with N2, 150C microwave for 30 min. LCMS showed completion. added DMF(3 mL), filtered through celite. concentrated. The residue was washed with EtOAc and water, MeoH to give about 55mg light brown solid

Quellen und Nachweise

ORD-Eintrag
ord-31892db8bbd04de79164da0921726b58
Quelldatensatz
750 AstraZeneca ELN dataset
Originallink
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