2-[(2,1,3-Benzothiadiazol-4-ylsulfonyl)amino]-5-chlorobenzoic acid → (+/-)-2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-5-chloro-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]=[CH:21][C:20]([Cl:23])=[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:25][C:26]1[CH:27]=[C:28]([CH:33]([CH3:36])[CH2:34][NH2:35])[CH:29]=[CH:30][C:31]=1[Cl:32]>>[N:1]1[S:5][N:4]=[C:3]2[C:6]([S:10]([NH:13][C:14]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:15]=3[C:16]([NH:35][CH2:34][CH:33]([C:28]3[CH:29]=[CH:30][C:31]([Cl:32])=[C:26]([Cl:25])[CH:27]=3)[CH3:36])=[O:18])(=[O:12])=[O:11])=[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)-5-chloro-benzoic acid and (±)-2-(3,4-dichloro-phenyl)-propylamine hydrochloride as in EXAMPLE 1, Part C. HPLC: RT=11.76 min. MS (ESI−): mass calcd. for C22H17Cl3N4O3S2, 553.98; m/z found, 553/555 [M−H]−. 1H NMR (400 MHz, CDCl3): 11.05 (s, 1H), 8.30 (dd, J=7.0, 1.0, 1H), 8.21 (d, 8.0, 1H), 7.70-7.66 (m, 1H), 7.65-7.63 (m, 1H), 7.41 (d, J=8.2, 1H), 7.29 (dd, J=4.6, 2.1, 2H), 7.05 (dd, J=9.6, 2.1, 2H), 5.80 (s, 1H), 3.67-3.60 (m, 1H), 3.32-3.26 (m, 1H), 3.02-2.97 (m, 1H), 1.30 (d, J=7.0, 3H).
Sources & evidence
- ORD record
- ord-809ab93e23124dfd82ab755c5f7013b9
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07855292B2
Reaction notes
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