8-Chloro-4-methyl-2-phenyl-3,4-dihydropyrido[3,2-F][1,4]oxazepin-5(2H)-one → 8-[3-Methoxy-4-(4-methylimidazol-1-yl)anilino]-4-methyl-2-phenyl-2,3-dihydropyrido[3,2-f][1,4]oxazepin-5-one

HRID 614

Reaction equation

HRID 614 reaction equation
CN1CC(c2ccccc2)Oc2nc(Cl)ccc2C1=O.COc1cc(N)ccc1-n1cnc(C)c1.Cl>CC(=O)O.CC(=O)O.COCCOC.O=C([O-])[O-].[Cs+].[Cs+].[Pd].c1ccc(-c2ccccc2P(C2CCCCC2)C2CCCCC2)cc1>COc1cc(Nc2ccc3c(n2)OC(c2ccccc2)CN(C)C3=O)ccc1-n1cnc(C)c1

Participants

7

Reactant 2

HCID 595778258-Chloro-4-methyl-2-phenyl-3,4-dihydropyrido[3,2-F][1,4]oxazepin-5(2H)-oneHCID 674242353-Methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline hydrochloride

Product 1

HCID 498200868-[3-Methoxy-4-(4-methylimidazol-1-yl)anilino]-4-methyl-2-phenyl-2,3-dihydropyrido[3,2-f][1,4]oxazepin-5-oneYield 40.02%

Reagents, catalysts & solvents 4

HCID 10796Cesium carbonateReagentHCID 27342162-(Dicyclohexylphosphino)biphenylCatalystHCID 4144353Palladium (II) acetateCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

were placed in a microwave vial equipped with a stirring bar. The vial was capped and flushed with argon. DME (2 mL) and Et3N (0.028 mL, 0.20 mmol) were added via a syringe and the mixture was stirred at room temperature for 30 min and then heated to 100°C in a microwave apparatus for 1h. The reaction mixture was diluted with dichloromethane and ethyl acetate, fitered and concentrated. The residue was purified by reversed phase HPLC to give 37 mg of the product as a solid.

Sources & evidence

ORD record
ord-322a5f0c927a43d5b08115d8443f975d
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Linked notes

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