N-(5-amino-2-cyclopropylphenyl)acetamide → N-[5-[[3-cyano-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidin-5-yl]amino]-2-cyclopropylphenyl]acetamide

HRID 737Notes

Reaction equation

HRID 737 reaction equation
CC(=O)Nc1cc(N)ccc1C1CC1.N#Cc1cnn2c(NC3COC3)cc(Cl)nc12>CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)C(C)(C)C)c(C(C)C)c1.CN(C)C=O.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]>CC(=O)Nc1cc(Nc2cc(NC3COC3)n3ncc(C#N)c3n2)ccc1C1CC1

Participants

7

Reactant 2

HCID 89098640N-(5-amino-2-cyclopropylphenyl)acetamideHCID 178418222HCID 178418222, compound

Product 1

HCID 72164289N-[5-[[3-cyano-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidin-5-yl]amino]-2-cyclopropylphenyl]acetamideYield 0%

Reagents, catalysts & solvents 4

HCID 10796Cesium carbonateReagentHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 11618717Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphaneCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Ref: _Angew. Chem. Int. Ed._ **2006** , _45_ , 6523-6527 1\. To a microwave tube was added N-(5-amino-2-cyclopropylphenyl)acetamide (0.038 g, 0.20 mmol), 5-chloro-7-(oxetan-3-ylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (0.060 g, 0.24 mmol), Cs2CO3 (0.196 g, 0.60 mmol), Pd2dba3 (0.018 g, 0.02 mmol), and di-tert-butyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (0.017 g, 0.04 mmol). The mixture was dissolved in DMF (0.5 mL) and sealed. The tube was de- gassed and inflated with N2. 2\. The reaction was heated at 90°C in oil-bath overnight. LCMS showed SM and byproducts and small amount of product mass. did not workup

Sources & evidence

ORD record
ord-6ca5406ed1914cc08b2221358d36ecf3
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Reaction notes

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