Hydrochloric Acid → HCID 178425709, compound

Participants

Reaction Steps

The compound of Example 382A (0.1 g, 0.19 mmol) was dissolved into 2 mL. of THF and cooled to 0° C. Lithium hydroxide (2 mLs, 0.5M) was slowly added to the reaction mixture and stirred for 3 Hrs. The pH was adjusted using 0.5 M HCl and a white precipitate was collected by vacuum filtration and purified twice by reverse phase preparative HPLC (Waters 25×10 cm, C-18 column, 220 nm UV detector, flow rate 15 mLs/min, linear gradient from 5% acetonitrile and 95% water containing 0.1% TFA to 60% acetonitrile in 40 minutes). Fractions containing pure compound were combined and lyophilized to yield the title compound (0.021 g, 18%) as a TFA salt: 1H NMR (300 MHz, methanol-d4) δ 8.04 (d, J=7.8 Hz, 1H), 7.79 (dd, J=7.3 Hz, 2H), 7.60-7.62 (m, 4H), 7.27-7.30 (m, 6H), 6.69 (dd, J=8.4 Hz, 1H), 6.63 (d, J=2.1, 1H) 4.42 (s, 2H), 4.19-4.26 (m, 1H), 2.14-2.32 (m, 2H), 1.98 (s, 3H), 1.75-1.87 (m, 2H).

Provenance & Evidence