Buchwald–Hartwig amination: 8-Chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine → N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-4-methyl-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.

• N-(4-(1H-imidazol-1-yl)phenyl)-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine41%
• 1-(8-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-2-(pyridin-3-yl)-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)ethanone35%
• (R)-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-6-methyl-8-phenyl-5,6,7,8-tetrahydropyrimido[5,4-f][1,4]oxazepin-2-amine30%
• (S)-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine28%
• N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-4-methyl-2-(pyridin-3-yl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine28%
• N-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]pyrimidin-2-amine19%
• 2-(2-(1,3-Dimethyl-1H-pyrazol-5-yl)-8-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)acetonitrile17%
• (R)-6-(2-fluoroethyl)-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-8-phenyl-5,6,7,8-tetrahydropyrimido[5,4-f][1,4]oxazepin-2-amine15%
• 1-(2-(Isopropoxymethyl)-8-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)ethanone15%
• (R)-2-(8-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-2-phenyl-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)acetonitrile8%
• 2-(Isopropoxymethyl)-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-4-methyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine5%
• 2-cyclopropyl-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-4-methyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepin-8-amine0%

Copied from the source record, unedited

8-chloro-4-methyl-2-phenyl-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (60.0 mg, 0.22 mmol), 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (57.7 mg, 0.28 mmol), palladium(II) acetate (4.90 mg, 0.02 mmol), 2-(Dicyclohexylphosphino)biphenyl (7.65 mg, 0.02 mmol) and CS2CO3 (213 mg, 0.66 mmol) were weighed into a microwave vial. The vial was capped and flushed with argon. DME (4 mL) was added and the mixture was heated to 100°C in a microwave apparatus for 1 h. The cooled reaction mixture was diluted with dichloromethane and methanol, filtered through a plug of Celite and the solvents were evaporated. The residue was purified by HPLC to give 36 mg (37 % Yield) of the title product.

This record comes from experimental reaction archive (ord-e759108cf109420c9b96a1936ea5e56d). Open the source and check it against what is on this page.

• experimental reaction archive record ord-e759108cf109420c9b96a1936ea5e56d 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.