1-Bromo-3-chloropropane → 3-Amino-6-(3-chloro-propyl)-4-thiophen-2-yl-6,7-dihydro-5H-1-thia-6,8-diaza-s-indacene-2-carboxylic acid amide

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-amino-4-thiophen-2-yl-6,7-dihydro-5H-1-thia-6,8-diaza-s-indacene-2-carboxylic acid amide hydrochloride (0.7 g, 2 mmol), 1-chloro-3-bromopropane (4 mmol), and triethylamine (2 ml) in 10 ml of anhydrous DMF was heated at 60° C. for 24 hours. The solvent was removed in vacuo, and the residue was purified by silica gel column (chloroform/methanol, 40:1) to give pure compound as a yellow solid. 1H-NMR (300 MHz, DMSO-d6): δ 7.88 (d, J=5.1 Hz, 1H), 7.29 (d, J=3.6 Hz, 1H), 7.27 (dd, J=3.6, 5.1 Hz, 1H), 7.22 (brs, 2H), 5.98 (brs, 2H), 4.00 (s, 2H), 3.77 (s, 2H), 3.67 (t, J=6.3 Hz, 2H), 2.78 (t, J=6.3 Hz, 2H), 1.90 (m, 2H). ES MS m/z 393, 395 (M+H)+.

Provenance & Evidence