1,1-Bis(methylthio)-2-nitroethylene → N-(3-{[1-(methylthio)-2-nitrovinyl]amino}phenyl)-3-[(quinolin-4-ylmethyl)amino]thiophene-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 1,1-bis(methylthio)-2-nitroethylene (1.4 g, 8.33 mmol) in MeOH (75 mL) was added N-(3-Aminophenyl)-3-[(quinolin-4-ylmethyl)amino]thiophene-2-carboxamide (2.1 g, 8.33 mmol) and the mixture was stirred at 85° C. overnight. The reaction mixture was cooled to rt and the yellow precipitate formed was filtered, washed with MeOH, and dried under vacuum to give N-(3-{[1-(methylthio)-2-nitrovinyl]amino}phenyl)-3-[(quinolin-4-ylmethyl)amino]thiophene-2-carboxamide as yellow solid. MS (ES): m/z 492.02 (100) [MH+]; 1H NMR (DMSO-d6, 400 MHz): δ 2.47 (s, 2H), 3.17 (d, J=5.6 Hz, 1H), 5.10 (d, J=5.2 Hz, 2H), 6.78 (s, 1H), 6.81 (d, J=5.2 Hz, 1H), 7.03 (d, J=8.0 Hz, 1H), 7.35-7.43 (m, 2H), 7.63 (d, J=5.2 Hz, 1H), 7.65-7.72 (m, 2H), 7.77-7.85 (m, 3H), 8.05-8.15 (m, 2H), 8.24 (dd, J=8.0, 7.2 Hz, 1H), 8.42 (d, J=4.0 Hz, 1H), 9.56 (s, 1H).

Provenance & Evidence