Water → HCID 178486593, compound

Participants

Reaction Steps

A light yellow solution of 3-(cyclopentylamino)-2-(3-methoxynaphthalen-2-yl)-1H-imidazo[1,2-b]pyrazole-7-carbonitrile (150 mg, 0.404 mmol) in DMSO (6 mL) was stored for 40 days at RT. Then, it was poured into a mixture of water and brine solution (˜150 mL) and the organic compound was extracted into ethyl acetate (2×50 mL). The combined extracts were washed with brine solution and dried over anhydrous MgSO4. Filtration and concentration gave the light yellow oil which was purified using an ISCO (40 g) column chromatography eluting with 0-60% ethyl acetate in hexanes. The desired fractions were combined and the solvent was removed under vacuum to isolate 36 mg (23% yield) of (E)-5-amino-1-(1-(cyclopentylimino)-2-(3-methoxynaphthalen-2-yl)-2-oxoethyl)-1H-pyrazole-4-carbonitrile as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ: 1.42-1.64 (br m, 4H), 1.64-1.80 (br, 4H), 3.75 (p, 1H), 3.77 (s, 3H), 7.45 (t, J=2.4 Hz, 1H), 7.48 (s, 1H), 7.64 (s, 1H), 7.65 (t, J=2.4 Hz, 1H) 7.88 (d, 1H), 8.10 (br s, 2H), 8.12 (d, 1H), 8.62 (s, 1H). LC/MS calcd. for C22H21N5O2 (m/e) 387.441, obsd. 388.0 (M+H, ES+).

Provenance & Evidence