6-Methoxy-5-(4-methyl-1H-imidazol-1-YL)pyridin-2-amine → HCID 57512844, compound

HRID 622

Reaction equation

HRID 622 reaction equation
COc1nc(N)ccc1-n1cnc(C)c1.Cc1cnc(C2CN(C)Cc3ccc(Cl)nc3O2)s1>CC(=O)O.CC(=O)O.COCCOC.O=C([O-])[O-].[Cs+].[Cs+].[Pd].c1ccc(-c2ccccc2P(C2CCCCC2)C2CCCCC2)cc1>COc1nc(Nc2ccc3c(n2)OC(c2ncc(C)s2)CN(C)C3)ccc1-n1cnc(C)c1

Participants

7

Conditions

Temperature
100 °C

Procedure

8-chloro-4-methyl-2-(5-methylthiazol-2-yl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (140 mg, 0.47 mmol), 6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-amine (106 mg, 0.52 mmol), 2-(DICYCLOHEXYLPHOSPHINO)BIPHENYL (16.59 mg, 0.05 mmol), PALLADIUM(II) ACETATE (10.63 mg, 0.05 mmol) and Cs2CO3 (308 mg, 0.95 mmol) were weighed into a microwave vial, the vial was capped and DME (4 mL) was added. The vial was flushed with argon and heated to 100°C in a microwave reactor for 1 h. The reaction mixture was diluted with dichloromethane and filtered and the solvents were evaporated. The residue was purified by column chromatography on Silica using gradient elution with methanol in dichloromethane (0-6 %) to give N-(6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl)-4-methyl-2-(5-methylthiazol-2-yl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine (162 mg, 73.8 %).

Sources & evidence

ORD record
ord-771383a2857c4cf6924928bdcc9bb648
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Linked notes

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