2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4,5-dichlorobenzoic acid → (+/-)-2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4,5-dichloro-N-[2-(3,4-dichloro-phenyl)-propyl]-benzamide
Reaction equation
[N:1]1[S:5][N:4]=[C:3]2[C:6]([S:10]([NH:13][C:14]3[CH:22]=[C:21]([Cl:23])[C:20]([Cl:24])=[CH:19][C:15]=3[C:16]([OH:18])=O)(=[O:12])=[O:11])=[CH:7][CH:8]=[CH:9][C:2]=12.Cl.[Cl:26][C:27]1[CH:28]=[C:29]([CH:34]([CH3:37])[CH2:35][NH2:36])[CH:30]=[CH:31][C:32]=1[Cl:33]>>[N:1]1[S:5][N:4]=[C:3]2[C:6]([S:10]([NH:13][C:14]3[CH:22]=[C:21]([Cl:23])[C:20]([Cl:24])=[CH:19][C:15]=3[C:16]([NH:36][CH2:35][CH:34]([C:29]3[CH:30]=[CH:31][C:32]([Cl:33])=[C:27]([Cl:26])[CH:28]=3)[CH3:37])=[O:18])(=[O:11])=[O:12])=[CH:7][CH:8]=[CH:9][C:2]=12Participants
3
Procedure
The title compound was prepared from 2-(benzo[1,2,5]thiadiazole-4-sulfonylamino)-4,5-dichloro-benzoic acid and (±)-2-(3,4-dichloro-phenyl)-propylamine hydrochloride as in EXAMPLE 1, Part C. HPLC: RT=12.51 min. MS (ESI−): mass calcd. for C22H16Cl4N4O3S2, 587.94; m/z found, 587/589/591 [M−H]. 1H NMR (500 MHz, CDCl3): 11.22 (s, 1H), 8.35 (d, J=7.0, 1H), 8.24 (d, J=8.8, 1H), 7.89 (s, 1H), 7.74-7.71 (m, 1H), 7.41 (d, J=8.2, 1H), 7.29 (d, J=2.0, 1H), 7.14 (s, 1H), 7.05 (dd, J=8.2, 2.0, 1H), 5.79 (s, 1H), 3.69-3.63 (m, 1H), 3.34-3.29 (m, 1H), 3.03-2.99 (m, 1H), 1.31 (d, J=7.0, 3H).
Sources & evidence
- ORD record
- ord-c0930200881f4c539c771a97d56d3c0c
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07855292B2
Reaction notes
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