HCID 169489376, compound → 4-[[(2S,4R)-1-(5-chloro-1-methylpyrazole-4-carbonyl)-2-methylpiperidin-4-yl]amino]-6,7-difluoro-1H-quinolin-2-one

HRID 533Notes

Reaction equation

HRID 533 reaction equation
C[C@H]1C[C@H](N)CCN1C(=O)c1cnn(C)c1Cl.O=C(O)C(F)(F)F.O=c1cc(Cl)c2cc(F)c(F)cc2[nH]1>CC(=O)O.CC(=O)O.Cc1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>C[C@H]1C[C@H](Nc2cc(=O)[nH]c3cc(F)c(F)cc23)CCN1C(=O)c1cnn(C)c1Cl

Participants

7

Reactant 2

HCID 169489376HCID 169489376, compoundHCID 178418196HCID 178418196, compound

Product 1

HCID 906824844-[[(2S,4R)-1-(5-chloro-1-methylpyrazole-4-carbonyl)-2-methylpiperidin-4-yl]amino]-6,7-difluoro-1H-quinolin-2-oneYield 49.46%

Reagents, catalysts & solvents 4

HCID 10796Cesium carbonateReagentHCID 634876Binap, (A+-)-CatalystHCID 4144353Palladium (II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

4-chloro-6,7-difluoroquinolin-2(1H)-one (100 mg, 0.46 mmol) was taken in a microwave tube. Added ((2S,4R)-4-amino-2-methylpiperidin-1-yl)(5-chloro-1-methyl-1H-pyrazol-4-yl)methanone 2,2,2-trifluoroacetate (172 mg, 0.46 mmol), followed by the addition of Palladium (II) acetate (10.41 mg, 0.05 mmol), racemic-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (28.9 mg, 0.05 mmol), Cesium carbonate (111 mL, 1.39 mmol), N,N'-Diisopropylethylamine (242 mL, 1.39 mmol). toluene (10 mL) was added and subjected to microwave with the following parameters. Temperature 140 °C Time 60 minutes After the completion of the reaction, dissolved the compound in methanol and purified by column

Sources & evidence

ORD record
ord-d1c1c91e4e404216818f2894a49b5c96
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Reaction notes

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