Formaldehyde → HCID 10210471, compound

Participants

Reaction Steps

The product from Example 93D (0.030 g, 0.0525 mmoles) in 1:1 CH3CN/MeOH (2 mL) was treated with 37% aqueous formaldehyde (0.020 mL, 0.263 mmoles) and sodium cyanoborohydride (0.008 g, 0.131 mmoles). Reaction mixed overnight at room temperature. Reaction quenched with two drops acetic acid and concentrated under reduced pressure. The residue was purified by preparative HPLC (CH3CN:0.1% TRIFLUOROACETIC ACID in H2O) on a YMC ODS Guardpak column to provide the title compound. 1H NMR (500 MHz, DMSO) δ8.96 (s, 1 H), 7.25 (m, 7 H), 7.20 (m, 1 H), 7.05 (m, 1 H), 6.97 (d, 2 H), 6.92 (d, 2 H), 6.70 (m, 1 H), 6.56 (dd, 1 H), 6.53 (dd, 1 H), 4.06 (s, 2 H), 4.03 (s, 2 H), 3.95 (m, 1 H), 3.50-3.80 (m, 1 H), 3.30-3.50 (m, 1 H), 3.00-3.20 (m, 2 H), 2.92 (s, 3 H), 2.80 (m, 5 H), 2.40 (s, 3 H), 2.00-2.30 (m, 1 H), 1.80 (m, 1 H); MS (ESI+) m/z 586 (M+H)+.

Provenance & Evidence