Buchwald–Hartwig amination: (2R)-8-chloro-4-methyl-2-phenyl-3,5-dihydro-2H-pyrido[3,2-f][1,4]oxazepine → (R)-4-Methyl-N-(5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl)-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine

Drawn from the record's atom map: which bonds break and which form between the reactants and products the source listed. It shows a change in connectivity, not a simulated trajectory and not a mechanism.

Temperature

100 °C

Only the dimensions the source stated are listed. Anything absent here was not recorded, and it is not inferred from what the class usually needs.

No other run in the library makes this product. These runs of the same class start from one of the same reactants, which is the nearest company this record has.

• gamma-Secretase modulator 6101%
• (R)-5-(2-Methoxy-6-(4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-ylamino)pyridin-3-yl)-1-methylpyridin-2(1H)-one35%
• (R)-N-(3-Methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine19%
• (R)-N-(6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl)-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine16%
• 4,6-Dimethyl-N-(5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl)-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine15%
• (R)-4-Methyl-N-(4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine0%
• gamma-Secretase modulator 632%
• (R)-4-Methyl-N-(4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine0%
• (R)-4-Methyl-N-(4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine0%
• (R)-4-Methyl-N-(4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine0%
• gamma-Secretase modulator 60%

Copied from the source record, unedited

(R)-8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (129 mg, 0.47 mmol), 5-(4-methyl-1H-imidazol-1-yl)pyridin-2-amine (82 mg, 0.47 mmol), PALLADIUM(II) ACETATE (10.54 mg, 0.05 mmol), 2-(DICYCLOHEXYLPHOSPHINO)BIPHENYL (16.46 mg, 0.05 mmol) and Cs2CO3 (229 mg, 0.70 mmol) were weighed into a microwave vial which was capped and flushed with argon. DME (5 mL) was added and the mixture was heated to 100°C in a microwave apparatus for 2 h. The mixture was filtered and purified by column chromatography on Silica using gradient elution with increasing concentration of methanol, from 0 to 6 %, in dichloromethane to give(R)-4-methyl-N-(5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl)-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine (69.5 mg, 35.9 %)

This record comes from experimental reaction archive (ord-2bf055ae52c14e578ca506139e6af8cb). Open the source and check it against what is on this page.

• experimental reaction archive record ord-2bf055ae52c14e578ca506139e6af8cb from dataset "750 AstraZeneca ELN dataset" (url: https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471). No atom mapping is provided by the source.

  experimental record · quality medium · source

experimental reaction record.