2-Acetylamino-4-aminotoluene → N-[5-[[3-cyano-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-yl]amino]-2-methylphenyl]acetamide

HRID 690

Reaction equation

HRID 690 reaction equation
CC(=O)Nc1cc(N)ccc1C.N#Cc1cnn2c(NC3CC3)cc(Cl)nc12>CC(=O)N(C)C.CC(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.[Na+].[Pd].[Pd].c1ccc(-c2ccccc2P(C2CCCCC2)C2CCCCC2)cc1>CC(=O)Nc1cc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)ccc1C

Participants

7

Reactant 2

HCID 794922-Acetylamino-4-aminotolueneHCID 898271735-Chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile

Product 1

HCID 72163809N-[5-[[3-cyano-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-yl]amino]-2-methylphenyl]acetamideYield 0%

Reagents, catalysts & solvents 4

HCID 23676156Sodium t-butoxideReagentHCID 27342162-(Dicyclohexylphosphino)biphenylCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

In a 25 mL round-bottomed flask (t=g) was 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (40 mg, 0.17 mmol), Pd2(dba)3 (7.84 mg, 8.56 µmol), and [Reactants] in DMA (1.5 mL) ([VOLUME]) to give a black suspension.[Reactants] and N-(5-amino-2-methylphenyl)acetamide (28.1 mg, 0.17 mmol) were added. stirred at 110C for 2 days. TLC showed major is SM, small amount of product was formed/ did not workup LCMS showed 349 mass ??

Sources & evidence

ORD record
ord-9d52138831044592b5c7c5511d53f49c
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Linked notes

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