2,3-Dichlorophenyl Isothiocyanate → 1-(2,3-Dichloro-phenyl)-3-(6'-fluoro-[2,3]bipyridinyl-3-ylmethyl)-thiourea
Reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]=[C:10]=[S:11].[F:12][C:13]1[N:18]=[CH:17][C:16]([C:19]2[C:24]([CH2:25][NH2:26])=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:15][CH:14]=1>>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][C:10]([NH:26][CH2:25][C:24]1[C:19]([C:16]2[CH:17]=[N:18][C:13]([F:12])=[CH:14][CH:15]=2)=[N:20][CH:21]=[CH:22][CH:23]=1)=[S:11]Participants
Procedure
The title compound was synthesized by general procedure 1 using 2,3-dichlorophenylisothiocyanate and C-(6′-fluoro-[2,3]bipyridinyl-3-yl)-methylamine (Example 192F) to give 0.974 g (72%) of 1-(2,3-dichloro-phenyl)-3-(6′-fluoro-[2,3]bipyridinyl-3-ylmethyl)-thiourea as a white powder. 1H NMR (DMSO-d6, 400 MHz) δ 4.74 (d, J=4.1 Hz, 2H), 7.31 (dd, J=2.5, J=8.2 Hz, 1H), 7.35 (t, J=8.2 Hz, 1H), 7.49 (dd, J=4.7 Hz, J=7.9 Hz, 1H), 7.53 (d, J=8.3 Hz, 1H), 7.87 (dd, J=1.5 Hz, J=7.9 Hz, 1H), 8.17 (dt, J=2.5 Hz, J=8.2 Hz, 1H), 8.39 (bs, 1H), 8.41 (d, J=2.5 Hz, 1H) 8.60 (dd, J=1.6 Hz, J=4.7 Hz, 1H), 9.49 (bs, 1H); RP-HPLC (Hypersil® HS C18, 5 μm, 100 Å, 25 cm; 5%-100% acetonitrile—0.1M ammonium acetate over 10 min, 1 mL/min), then 100% acetonitrile isocratic 2 minutes, Rt 10.30 min. (94.3%); MS: M+H+ 407.
Sources & evidence
- ORD record
- ord-8e4ab80d028e4dc7b145c075afcbb08f
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08546374B2
Reaction notes
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