Formaldehyde → HCID 86292429, compound

Participants

Reaction Steps

A solution of Example 88C (15 mg, 0.04 mmol) in methanol (2 mL) was treated with 37% formaldehyde in water (12 mg, 0.4 mmol) and the mixture was stirred at room temperature for 1 hour. Sodium cyanoborohydride (5 mg, 0.08 mmol) was added and the mixture was stirred at room temperature for 12 hours. The mixture was diluted with dichloromethane and washed with water. The organic phase was concentrated and purified by HPLC (Zorbax C-18, using a 0-100% gradient of water/acetonitrile, containing 0.1% trifluoroacetic acid) to afford the title compound. 1H NMR (400 MHz, DMSO-d6): δ 1.17-1.38 (m, 2H), 1.64-1.73 (m, 2H), 1.77-1.96 (m, 4H), 2.34 (d, J=13.56 Hz, 4H), 2.83 (d, J=4.75 Hz, 3H), 3.00-3.20 (m, 4H), 3.56 (d, J=11.53 Hz, 2H), 3.88 (dd, J=10.68, 3.22 Hz, 2H), 6.68 (d, J=8.48 Hz, 1H), 6.77-6.83 (m, 1H), 7.18 (d, J=7.80 Hz, 1H), 7.50 (d, J=5.09 Hz, 1H), 7.58-7.63 (m, 1H), 8.24-8.27 (m, 1H). LCMS: 406 (M+H)+.

Provenance & Evidence