Buchwald–Hartwig amination: 2-[(2,5-dichloro-4-pyridinyl)amino]-N-(methyloxy)benzamide → 2-({5-Chloro-2-[(1,3-dimethyl-1H-pyrazol-4-yl)-amino]-4-pyridinyl}amino)-N-(methyloxy)benzamide

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

150 °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.

• 6-[(1,3-Dimethylpyrazol-4-yl)amino]-4-[(2-methyl-1-oxo-3,4-dihydroisoquinolin-8-yl)amino]pyridine-3-carbonitrile55%
• 2-({5-Chloro-2-[(1,3-dimethyl-1h-pyrazol-4-yl)amino]-4-pyridinyl}amino)-n-methylbenzamide53%
• 2-[[5-cyano-2-[(1,3-dimethylpyrazol-4-yl)amino]-4-pyridinyl]amino]-N-methylbenzamide50%
• Gsk-225609847%
• 6-[(1,3-Dimethylpyrazol-4-yl)amino]-4-[(2-methyl-1-oxo-3,4-dihydroisoquinolin-8-yl)amino]pyridine-3-carbonitrile44%
• Gsk-225609836%
• Gsk-225609834%
• 2-[[2-[(1,3-dimethylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyridin-4-yl]amino]-N-methylbenzamide34%
• 2-[[2-[(1,3-dimethylpyrazol-4-yl)amino]-5-(trifluoromethyl)-4-pyridyl]amino]-N-methoxy-benzamide11%
• 6-[(1,3-Dimethylpyrazol-4-yl)amino]-4-[(2-methyl-1-oxo-3,4-dihydroisoquinolin-8-yl)amino]pyridine-3-carbonitrile7%

Copied from the source record, unedited

2-(2,5-dichloropyridin-4-ylamino)-N-methoxybenzamide (250 mg, 0.80 mmol), 1,3-dimethyl-1H-pyrazol-4-amine (134 mg, 1.20 mmol), Sodium tert-butoxide (115 mg, 1.20 mmol), 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (55.6 mg, 0.10 mmol) and BIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (58.7 mg, 0.06 mmol) were suspended in dioxane (15 mL) and sealed into a microwave tube. The reaction was heated to 150 °C for 30 minutes in the microwave reactor and cooled to RT. Reaction not complete by LCMS so more 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (55.6 mg, 0.10 mmol), BIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (58.7 mg, 0.06 mmol) and 1,3-dimethyl-1H-pyrazol-4-amine (134 mg, 1.20 mmol) were added and the reaction heated to 150 ºC for a further 30 minutes in the microwave reactor and cooled to RT.

This record comes from experimental reaction archive (ord-48707410a8f646d7ad65813e3cef2505). Open the source and check it against what is on this page.

• experimental reaction archive record ord-48707410a8f646d7ad65813e3cef2505 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.