Buchwald–Hartwig amination: 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline → (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)acetonitrile

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-(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-amine37%
• 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%
• 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%
• (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-amine15%

Copied from the source record, unedited

3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (195 mg, 0.96 mmol), (R)-2-(8-chloro-2-phenyl-2,3-dihydropyrido[3,2-f][1,4]oxazepin-4(5H)-yl)acetonitrile (288 mg, 0.96 mmol) Palladium acetate (21.55 mg, 0.10 mmol) and Cesium carbonate (938 mg, 2.88 mmol) were added in a microwave vial. The mixture was capped and flushed with argon. 1,2-dimethoxyethane (5 mL) was added, the reaction mixture was flushed with argon and the mixture was run in a microwave for 60 minutes at 100°C. Only after two additional additions of catalyst and ligand with 3h extra runtime was the reaction complete. The reaction mixture was filtrated through Celite and washed with dichloromethane. The filtrate was concentrated and the crude product was purified by preparative chromatography 3 times yielding (R)-2-(8-(3-methox

This record comes from experimental reaction archive (ord-64de42ce56244836b512746d4c6a3fee). Open the source and check it against what is on this page.

• experimental reaction archive record ord-64de42ce56244836b512746d4c6a3fee 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.