Benzene, 1-chloro-3-isocyanato- → 1-(3-Chloro-phenyl)-3-{5-[2-(6-cyano-thieno[3,2-b]pyridin-7-ylamino)-ethyl]-thiazol-2-yl}-urea
Reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH2:7][CH2:8][NH:9][C:10]2[C:15]([C:16]#[N:17])=[CH:14][N:13]=[C:12]3[CH:18]=[CH:19][S:20][C:11]=23)=[CH:5][N:6]=1.[Cl:21][C:22]1[CH:23]=[C:24]([N:28]=[C:29]=[O:30])[CH:25]=[CH:26][CH:27]=1>ClCCl>[Cl:21][C:22]1[CH:23]=[C:24]([NH:28][C:29]([NH:1][C:2]2[S:3][C:4]([CH2:7][CH2:8][NH:9][C:10]3[C:15]([C:16]#[N:17])=[CH:14][N:13]=[C:12]4[CH:18]=[CH:19][S:20][C:11]=34)=[CH:5][N:6]=2)=[O:30])[CH:25]=[CH:26][CH:27]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 7-[2-(2-amino-thiazol-5-yl)-ethylamino]-thieno[3,2-b]pyridine-6-carbonitrile (27.1 mg, 0.09 mmol) in 2 ml of dichloromethane was added 3-chloro phenyl isocyanate (0.02 ml, 0.16 mmol). The resulting mixture was stirred at room temperature for 16 hr and filtered. Solids were washed with CH2Cl2, and the combined organics were concentrated. The residue was purified by chromatography on TLC plate with MeOH/CH2Cl2/NH3(aq)=1/20/0.1 to give 5.6 mg (14%) of a white solid. 1H NMR (400 MHz, CD3OD) δ 8.41 (s, 1H), 8.06 (d, J=5.6 Hz, 1H), 7.62-7.66 (m, 1H), 7.43 (d, J=5.2 Hz, 1H), 7.25-7.31 (m, 2H), 7.16 (s, 1H), 7.00-7.07 (m, 1H), 4.06 (t, J=7.2 Hz, 2H), 3.20 (t, J=7.2 Hz, 2H). LC-MS (ESI) m/z 455.0 (M+1).