Dimethylamine → HCID 89662837, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of Example 164 (90 mg; 0.22 mmol; 1 eq.), a 2M solution of dimethylamine in THF and sodium triacetoxyborohydride (59 mg; 0.28 mmol; 1.3 eq.) in DCE (2 mL) was stirred at 50° C. for 1 hour whereupon triacetoxyborohydride (59 mg; 0.28 mmol; 1.3 eq.) was added. The resulting mixture was stirred at 70° C. for 3 hours then diluted with ethyl acetate. The solution was washed with 0.1M NaOH, dried over sodium sulfate and concentrated in vacuo. Purification by column chromatography (EA to 10 MeOH in EA) afforded the title compound (27 mg, 28%) as a white solid. 1H NMR (DMSO-d6) δ 7.42-7.26 (m, 1H), 7.09 (d, J=11.5 Hz, 1H), 6.86 (t, J=8.2 Hz, 1H), 4.78 (d, J=7.9 Hz, 2H), 4.59 (d, J=15.0 Hz, 2H), 4.13-3.89 (m, 2H), 2.92-2.74 (m, 4H), 2.61 (s, 1.4H), 2.56 (s, 1.6H), 2.06 (s, 6H), 0.95-0.78 (m, 3H). HPLC (max plot) 99.9%, Rt 2.77 min. UPLC/MS: (MS+) 446.3 ([M+H]+).

Provenance & Evidence