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

HRID 1435596Notes

Reaction equation

CS[C:3]([S:8][CH3:9])=[CH:4][N+:5]([O-:7])=[O:6].[NH2:10][C:11]1[CH:12]=[C:13]([NH:17][C:18]([C:20]2[S:21][CH:22]=[CH:23][C:24]=2[NH:25][CH2:26][C:27]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[N:30]=[CH:29][CH:28]=2)=[O:19])[CH:14]=[CH:15][CH:16]=1>CO>[CH3:9][S:8][C:3]([NH:10][C:11]1[CH:12]=[C:13]([NH:17][C:18]([C:20]2[S:21][CH:22]=[CH:23][C:24]=2[NH:25][CH2:26][C:27]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[N:30]=[CH:29][CH:28]=2)=[O:19])[CH:14]=[CH:15][CH:16]=1)=[CH:4][N+:5]([O-:7])=[O:6]

Participants

Conditions

Temperature: 85 °C

Procedure

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).

Workup

temperatureThe reaction mixture was cooled to rt
customthe yellow precipitate formed
filtrationwas filtered
washwashed with MeOH
customdried under vacuum

Sources & evidence

ORD record: ord-b6183043431f4bb8952d7b87729a94a5
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07618965B2

Reaction notes

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