Triethylamine → 1-(3-chloro-4-methoxyphenyl)-N-(6'-methoxy-3,5'-dimethyl-2,3'-bipyridin-6-yl)cyclopropanecarboxamide

To a solution of 1-(3-chloro-4-methoxyphenyl)cyclopropanecarboxylic acid (45.3 mg, 0.2 mmol) in dichloromethane (2 mL) was added thionyl chloride (43.8 μL, 0.60 mmol) followed by DMF (1 drop) and the reaction was stirred at room temperature for 30 minutes and then the solvent was evaporated. Toluene (˜1 mL) was added and mixed with the residue and then evaporated. The residue 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 Et3N (83.6 μL, 0.60 mmol) in dichloromethane (1 mL) was added. The reaction was stirred at room temperature for 12 hours and then the reaction was then concentrated. The residue was dissolved in DMSO and purified by HPLC (10-99% acetonitrilein water) to yield 44 mg of the product. ESI-MS m/z calc. 437.1. found 438.1 (M+1)+. Retention time 2.10 minutes.

1. customthe solvent was evaporated
2. additionToluene (˜1 mL) was added
3. additionmixed with the residue
4. customevaporated
5. dissolutionThe residue was then dissolved in dichloromethane (1 mL)
6. stirringThe reaction was stirred at room temperature for 12 hours
7. concentrationthe reaction was then concentrated
8. dissolutionThe residue was dissolved in DMSO
9. custompurified by HPLC (10-99% acetonitrilein water)

ORD record

ord-cd9cd6bf06cd4aceb1d5d3ea73ef9972

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08969386B2