Isopropanol → Isopropyl 3-{[(5-chloro-3-methyl-1-benzothien-2-yl)sulfonyl]amino}benzoate
Reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10]([NH:13][C:14]3[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=3)[C:17]([OH:19])=[O:18])(=[O:12])=[O:11])=[C:7]([CH3:23])[C:6]=2[CH:24]=1.[CH:25](O)([CH3:27])[CH3:26]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10]([NH:13][C:14]3[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=3)[C:17]([O:19][CH:25]([CH3:27])[CH3:26])=[O:18])(=[O:12])=[O:11])=[C:7]([CH3:23])[C:6]=2[CH:24]=1Participants
3
Procedure
The product was prepared from 3-{[(5-chloro-3-methyl-1-benzothien-2-yl)sulfonyl]amino}benzoic acid (21 mg, 0.055 mmol) (Intermediate 19) and isopropyl alcohol (6.0 mg, 0.100 mmol) according to the General Procedure 7, described in Example 107, using a slightly modified reaction time (2 days). The title compound was obtained in 57% yield (13.3 mg). 1H NMR (500 MHz, CDCl3) δ ppm 1.30 (d, J=6.32 Hz, 6 H) 2.45 (s, 3 H) 5.18 (spt, J=6.32 Hz, 1 H) 6.89 (s, 1 H) 7.35 (dd, J=8.06, 7.65 Hz, 1 H) 7.41 (ddd, J=8.06, 2.35, 1.18 Hz, 1 H) 7.44 (dd, J=8.73, 1.94 Hz, 1 H) 7.68 (dd, J=2.35, 1.50 Hz, 1 H) 7.71 (dd, J=8.73, 0.61 Hz, 1 H) 7.71 (dd, J=1.94, 0.61 Hz, 1 H) 7.83 (ddd, J=7.65, 1.50, 1.18 Hz, 1 H). MS (ESI+) m/z 424 [M+H]+.