Water → HCID 178425485, compound

Participants

Reaction Steps

NaCNBH4 (15.5 mg, 0.25 mmol) was added to a solution of Example 183 (32.1 mg, 0.1 mmol) in CH2Cl2-MeOH (2 mL) containing sodium acetate (12.3 mg, 0.15 mmol) and p-methyl benzaldehyde (14.4 mg, 0.12 mmol) at 0° C. The resulting suspension was stirred overnight and water (50 mL) was slowly added and the mixture extracted with CH2Cl2 (3×50 mL). The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The resulting material was purified by LCMS (acetonitrile-water gradient) to give the title compound (20 mg, 45%) as a white solid. 1H NMR (400 MHz, chloroform-d) δ ppm 2.27 (s, 3H) 4.3 (s, 2H) 7.01 (t, J=5.21 Hz, 1 H) 7.08 (d, J=5.11 Hz, 2 H) 7.13 (dd, J=7.21, 4.42, Hz, 1 H) 7.25 (dd, J=5.27, 3.48 Hz, 1 H) 7.39 (t, J=5.11 Hz, 1 H) 7.46 (t, J=5.11 Hz, 1 H) 7.58 (d, J=5.11 Hz, 2 H) 7.68 (dd, J=9.21, 5.42, Hz, 1 H) 8.76 (d, J=5.91 Hz, 1 H) 8.82 (d, J=5.91 Hz, 1 H). MS (ES) [M+H] calculated for C25H21ClN5, 426.14; found 426.09.

Provenance & Evidence