Potassium Carbonate → HCID 178505083, compound

Participants

Reaction Steps

A 2 mL CH2Cl2 suspension of 0.05 g (0.11 mmol) 4-(cyclohexylamino)-8-[3-(aminomethyl)benzyl]-1-(3-fluorophenyl)-1,3,8-triazaspiro[4.5]dec-3-en-2-one (Example (7-12)), 0.02 mL (0.22 mmol) methanesulfonyl chloride and excess K2CO3 was allowed to stir at rt overnight. The reaction was filtered and concentrated. The remaining oil was dissolved in 0.5 mL CH2Cl2 and purified on an Isco automated system affixed with a Biotage Flash 25(S) cartridge eluted at 20 mL/min with 0-5% MeOH in CH2Cl2 over 15 min and hold at 5% MeOH for 30 min. The product eluted second, pure by HPLC/MS and NMR. 1H NMR (400 MHz, CDCl3) δ 7.79-7.83 (m, 1H), 7.45-7.54 (m, 2H), 7.33-7.4 (m, 2H), 7.12-7.14 (m, 1H), 6.96-7.05 (m, 3H), 4.31-4.39 (m, 1H), 3.92-4.05 (m, 1H), 3.48-3.52 (m, 1H), 2.65-2.80 (m, 2H), 2.4-2.50 (m, 2H), 1.90-2.20 (m, 6H), 1.62-1.8 (m, 4H), 1.55 (s, 3H), 1.30-1.50 (m, 2H), 1.15-1.30 (m, 4H). MS 542.4

Provenance & Evidence