Ammonia → HCID 72705236, compound

Participants

Reaction Conditions

Reaction Steps

Methanolic ammonia (7 M, 1.89 mL, 13.2 mmol) and toluene (2 mL) was added to di-tert-butyl [5′-fluoro-6′-(3-fluoropropoxy)-4-methoxy-5″-methyl-3′H-dispiro[cyclohexane-1,2′-indene-1′,2″-imidazol]-4″-yl]imidodicarbonate (Intermediate 16, 260 mg, 0.44 mmol). The mixture was transferred to a MW vial which was capped and heated to 85° C. for a week. The mixture was concentrated and partitioned between EtOAc and 2 M citric acid. The phases were separated and the organic phase was discarded. The aqueous phase was basified by addition of 50% aq. NaOH solution to pH 12 and then extracted with EtOAc. The combined organic phases were treated with charcoal, filtered through diatomaceous earth and concentrated. Purification of the residue by preparative HPLC afforded the title compound (17 mg, 10% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 0.83-0.95 (m, 1 H) 1.07-1.26 (m, 2 H) 1.33-1.49 (m, 3 H) 1.76-1.85 (m, 2 H) 1.97-2.11 (m, 2 H) 2.13-2.19 (m, 3 H) 2.82-2.99 (m, 3 H) 3.18 (s, 3 H) 3.90-4.01 (m, 2 H) 4.51 (t, 1 H) 4.61 (t, 1 H) 6.26 (d, 1 H) 6.53 (s, 2 H) 7.13 (d, 1 H); MS (ES+) m/z 392 [M+H]+.

Provenance & Evidence