Dimethyl Sulfoxide → (1S,3R)-3-(5'-chloro-6-(3-fluorobenzylamino)-2,4'-bipyridin-2'-yl-amino)cyclopentanecarbaldehyde

Temperature

-78 °C

In a flame-dried argon purged 20 mL conical flask, oxalyl chloride (0.025 ml, 0.281 mmol) was dissolved in DCM (0.5 ml) and cooled to −78° C. under argon. DMSO (0.030 ml, 0.422 mmol) was dissolved in DCM (0.5 ml) and added dropwise to the previous solution (I don't see issues here). This was stirred for 30 min at −78° C. ((1S,3R)-3-(5′-chloro-6-(3-fluorobenzylamino)-2,4′-bipyridin-2′-yl-amino)cyclopentyl)methanol (60 mg, 0.141 mmol) was dissolved in DCM (0.5 ml) and added dropwise to the reaction mixture. The resulting mixture was stirred for 60 min at −78° C. TEA (0.078 ml, 0.562 mmol) was dissolved in DCM (0.5 ml) and added dropwise to the reaction mixture, after which the reaction mixture was allowed to stir and warm to ambient temp over 2 hr. The reaction mixture was diluted with EtOAc, washed with saturated NH4Cl (30 mL×3), H2O (30 mL), brine (30 mL), dried over Na2SO4 and reduced. The resulting residue was used without further purification. LCMS (m/z): 425.2 (MH+), retention time=0.72.

1. customIn a flame-dried argon purged 20 mL conical flask
2. additionadded dropwise to the previous solution (I
3. additionadded dropwise to the reaction mixture
4. additionadded dropwise to the reaction mixture
5. stirringto stir
6. temperaturewarm to ambient temp over 2 hr
7. washwashed with saturated NH4Cl (30 mL×3), H2O (30 mL), brine (30 mL)
8. dry with materialdried over Na2SO4
9. customThe resulting residue was used without further purification

ORD record

ord-5a9ad26113df494bb8a30aa9558e557c

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08778951B2