Sodium borohydride → HCID 86690353, compound

Participants

Reaction Conditions

Reaction Steps

To a round bottom flask was added 4-((S)-3-(((1R,2R)-2-((4-formylpyridin-2-yl)amino)cyclohexyl)amino)piperidin-1-yl)benzonitrile (100 mg, 0.248 mmol) and THF (1 mL). The reaction was cooled to 0° C. and NaBH4 (9.38 mg, 0.248 mmol) was added to the reaction. The reaction was stirred at 0° C. for 2 hrs. The reaction was quenched with 1N NH4Cl (0.5 ml) and then diluted with EtOAc (30 ml). The organics was washed with water (2×15 ml) and saturated NaCl solution (15 ml). The organic layer dried over MgSO4, filtered and concentrated. The residue was purified using ISCO system (0-100% EtOAc/Hex) to give 4-((S)-3-(((1R,2R)-2-((4-(hydroxymethyl)pyridin-2-yl)amino)cyclohexyl)amino)piperidin-1-yl)benzonitrile (23 mg, 0.054 mmol, 21.74% yield) as white solid. Anal. Calcd. for C24H31N5O m/z 405.3, found: 406.2 (M+H)+; 1H NMR (400 MHz, METHANOL-D4) δ ppm 8.07-7.97 (m, 1H), 7.45 (d, J=8.8 Hz, 2H), 6.93 (d, J=9.3 Hz, 3H), 6.62-6.51 (m, 1H), 4.60 (s, 2H), 3.86-3.75 (m, 1H), 3.71-3.62 (m, 1H), 3.37-3.33 (m, 1H), 2.95-2.84 (m, 1H), 2.83-2.59 (m, 3H), 2.16-2.04 (m, 2H), 2.01-1.92 (m, 1H), 1.82-1.72 (m, 2H), 1.68-1.55 (m, 1H), 1.45-1.23 (m, 6H).

Provenance & Evidence