HCID 58423331, compound → HCID 58423095, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of (Z)-5-(2-(3-(dimethylamino)pyrrolidin-1-yl)-5-nitrobenzylidene)thiazolidine-2,4-dione (100 mg, 0.28 mmol) (Method 149) and iron (154 mg, 2.76 mmol) chip in MeOH (10 mL) was added 5 drops of conc. HCl and 5 drops of water. The mixture was stirred at 80° C. for 1 hr. The mixture was loaded into silica gel, purified with ISCO (100% ethyl acetate to methanol/ethyl acetate=50%) to yield a red solid which was repurified with Gilson (acetonitrile:water:0.1% TFA=0% to 50% fro 7 min) to yield a yellow solid as (Z)-5-(5-amino-2-(3-(dimethylamino)pyrrolidin-1-yl)benzylidene)thiazolidine-2,4-dione (51.0 mg, 38.6%). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.55 (brs, 1 H), 11.32 (brs, 1 H), 10.30 (brs, 2 H), 7.80 (s, 1 H), 7.42 (m, 2 H), 7.19 (m, 1 H), 3.95 (m, 1 H), 3.39-3.27 (m, 4 H), 2.78 (s, 6 H), 2.30-2.10 (m, 2 H); m/z 333.

Provenance & Evidence