HCID 178425489, compound → HCID 178425488, compound

Participants

Reaction Steps

N2′-(trans-4-aminocyclohexyl)-5′-chloro-N6-(((R/S)-2,2-dimethyltetrahydro-2H-pyran-4-yl)methyl)-2,4′-bipyridine-2′,6-diamine trifluoroacetic acid salt was dissolved in MeOH (2 mL) and filtered through VariPure™ IPE [500 mg per 6 mL tube; 0.9 mmol (nominal); part no.: PL3540-C603VP], eluted with MeOH (6 mL) and concentrated in vacuo providing N2′-(trans-4-aminocyclohexyl)-5′-chloro-N6-(((R/S)-2,2-dimethyltetrahydro-2H-pyran-4-yl)methyl)-2,4′-bipyridine-2′,6-diamine as a colorless oil. Yield: 20 mg. The enantiomers were resolved by chiral HPLC [Chiralpak AD column 21×50 mm, 20 mic; 20 mg/2 mL EtOH; heptane/IP A; 85:15 (v:v); 20 mL/min, 330 psi]. Fraction 1: White solid. Yield: 7.2 mg. Retention time: 10.4 min. [Chiralpak AD-H, column 4.6×100 mm, 5 mic; 20 mg/2 mL EtOH; heptane/IPA; 85:15 (v:v); 1 mL/min]. 1H NMR (400 MHz, METHANOL-d4) δ [ppm]1.07-1.18 (m, 2 H) 1.20 (s, 3 H) 1.21 (s, 3 H) 1.23-1.41 (m, 4 H) 1.65-1.74 (m, 2 H) 1.90-1.99 (m, 2 H) 2.09 (m, 3 H) 2.71 (br. s., 1H) 3.19 (d, J=6.65 Hz, 2 H) 3.57-3.67 (m, 1 H) 3.67-3.74 (m, 2 H) 6.52 (d, 1 H) 6.61 (s, 1 H) 6.71 (d, 1 H) 7.42-7.50 (m, 1 H) 7.94 (s, 1 H).

Provenance & Evidence