Formic Acid → HCID 71116047, compound

Participants

Reaction Conditions

Reaction Steps

To an orange solution containing 3-(((7-ethyl-3-neopentyl-2-oxo-1-oxa-3-azaspiro[4.5]decan-7-yl)methyl)amino)-4-nitrobenzonitrile (0.125 g, 0.292 mmol) in MeOH (2.48 mL) was added iron (325 mesh) (0.163 g, 2.92 mmol), trimethyl orthoformate (0.322 mL, 2.92 mmol), and formic acid (0.112 mL, 2.92 mmol). The reaction mixture was stirred at 65° C. for 21 h. Additional trimethyl orthoformate ((0.322 mL, 2.92 mmol) and formic acid (0.112 mL, 2.92 mmol) were added, and the reaction was stirred at 65° C. for another 4 h. The reaction was cooled to rt, diluted with MeCN (2 mL), and filtered through a Acrodisc CR 25 mm syringe filter with 0.2 μm PTFE membrane. The filtered solution was purified by reverse-phase HPLC (Sunfire Prep C18 column (30×150 mm); 15 min run; 25 mL/min elution; Solvent A: MeCN/0.1% TFA, Solvent B: water/0.1% TFA, gradient: 30-60% solvent A) to afford the title compound (0.139 g, 88% yield) as the TFA salt. 1H NMR (400 MHz, CDCl3) δ 8.65 (s, 1H), 8.06 (d, J=8.53 Hz, 1H), 7.85 (s, 1H), 7.73 (dd, J=1.25, 8.53 Hz, 1H), 4.13 (s, 2H), 3.31 (dd, J=8.78, 22.84 Hz, 2H), 3.00 (dd, J=14.31, 38.15 Hz, 2H), 2.01 (d, J=13.55 Hz, 2H), 1.81-1.97 (m, 2H), 1.58-1.75 (m, 3H), 1.10-1.29 (m, 3H), 1.06 (t, J=7.40 Hz, 3H), 0.96 (s, 9H); MS (m/z) 409.2 (M+H+).

Provenance & Evidence