Reaktion #157

ord-23579b28ef824d8ba8083ac0e9a7b70a

Reaktionsgleichung

CNC(=O)c1ccccc1Nc1cc(Cl)ncc1Cl
CNC(=O)c1ccccc1Nc1cc
Cc1nn(C)cc1N
Cc1nn(C)cc1N
CNC(=O)c1ccccc1Nc1cc(Nc2cn(C)nc2C)ncc1Cl
CNC(=O)c1ccccc1Nc1cc
Ausbeute 53.3%

Lösungsmittel

Reaktionsbedingungen

Temperatur
150°CELSIUS

Vorschrift

1,3-dimethyl-1H-pyrazol-4-amine (180 mg, 1.62 mmol), 2-(2,5-dichloropyridin-4-ylamino)-N-methylbenzamide (400 mg, 1.35 mmol), Sodium t-Butoxide (156 mg, 1.62 mmol),(R)-(-)-1-[(S)-2-(DICYCLOHEXYLPHOSPHINO)FERROCENYL]ETHYLDI-T- BUTYLPHOSPHINE (73.8 mg, 0.14 mmol) and diacetoxypalladium (24.26 mg, 0.11 mmol) were suspended in DME (8 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. Incomplete reaction, the reaction was heated to 150 °C for a further 1 hour in the microwave reactor and cooled to RT. The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3/MeOH and fractions were evaporated to dryness. The crude product was then purified by Basic prep HPLC, fractions containing the desired compound were evaporated to dryness to afford 2-(5-chloro-2-(1,3-dimethyl-1H-pyrazol-4-ylamino)pyridin-4-ylamino)-N-methylbenzamide (267 mg, 53.3 %) as a brown solid.

Quelle

750 AstraZeneca ELN dataset