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 534Notes

Reaction equation

HRID 534 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 23.08%

Reagents, catalysts & solvents 4

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

Conditions

Temperature
140 °C

Procedure

((2S,4R)-4-amino-2-methylpiperidin-1-yl)(5-chloro-1-methyl-1H-pyrazol-4-yl)methanone 2,2,2-trifluoroacetate (1548 mg, 4.17 mmol) was taken in a 100ml single necked flask equipped with a reflux condenser connected to nitrogen source. Added 4-chloro-6,7-difluoroquinolin-2(1H)-one (600 mg, 2.78 mmol), followed by the addition of racemic-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (173 mg, 0.28 mmol), Palladium (II) acetate (62.5 mg, 0.28 mmol), and Cesium carbonate (668 mL, 8.35 mmol). toluene (60 mL) was added followed by the addition of N,N'-Diisopropylethylamine (1454 mL, 8.35 mmol). The contents of the flask were purged with nitrogen for 5 minutes and heate at 140 °C for overnight. After the completion of the reaction, added methanol, and adsorbed on silica gel, and purified by reverse phase column.

Sources & evidence

ORD record
ord-eddc21aec4f145cea425a3b68c05d6df
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Reaction notes

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