Triethylamine → n-(6'-Methoxy-3,5'-dimethyl-2,3'-bipyridin-6-yl)-1-(3-methoxyphenyl)cyclopropanecarboxamide

1-(3-Methoxyphenyl)cyclopropanecarboxylic acid (38.4 mg, 0.2 mmol) was dissolved in dichloromethane (2 mL) and thionyl chloride (43.8 μL, 0.60 mmol) was added followed by DMF (1 drop) and the reaction was stirred at room temperature for 30 minutes. Then the solvent was removed by evaporation, toluene (˜1 mL) was added twice, mixed with the residue and removed by evaporation and then the residue was placed under high vacuum for 10 minutes. It was then dissolved in dichloromethane (1 mL) and a solution of 6′-methoxy-3,5′-dimethyl-2,3′-bipyridin-6-amine (45.9 mg, 0.20 mmol) and triethyl amine (83.6 μL, 0.60 mmol) in dichloromethane (1 mL) was added. The reaction was stirred at room temperature for 12 hours. The reaction was then concentrated. The residue was dissolved in DMSO and purified by reverse phase HPLC (10-99% CH3CN in water) to yield 41 mg (50% yield) of the product. ESI-MS m/z calc. 403.5. found 404.5 (M+1)+. Retention time 2.03 minutes.

1. customThen the solvent was removed by evaporation, toluene (˜1 mL)
2. additionwas added twice
3. additionmixed with the residue
4. customremoved by evaporation
5. waitthe residue was placed under high vacuum for 10 minutes
6. dissolutionIt was then dissolved in dichloromethane (1 mL)
7. stirringThe reaction was stirred at room temperature for 12 hours
8. concentrationThe reaction was then concentrated
9. dissolutionThe residue was dissolved in DMSO
10. custompurified by reverse phase HPLC (10-99% CH3CN in water)

ORD record

ord-739a9389c05c47c68836835f3aa21605

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08969386B2