4-acetyl-N-(5-methylisoxazole-3-yl)benzenesulfonamide → 4-[3E-(2,4-Dimethoxy-5-pyrrolidin-1-yl-phenyl)acryloyl]-N-(5-methyl-isoxazol-3-yl)benzenesulfonamide
Reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:18]=[C:17]([CH3:19])[O:16][N:15]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH3:20][O:21][C:22]1[CH:29]=[C:28]([O:30][CH3:31])[C:27]([N:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)=[CH:26][C:23]=1[CH:24]=O>>[CH3:20][O:21][C:22]1[CH:29]=[C:28]([O:30][CH3:31])[C:27]([N:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)=[CH:26][C:23]=1/[CH:24]=[CH:2]/[C:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([NH:13][C:14]2[CH:18]=[C:17]([CH3:19])[O:16][N:15]=2)(=[O:11])=[O:12])=[CH:8][CH:9]=1)=[O:3]Participants
3
Procedure
The title compound was prepared in a similar manner as Ex-1 using 4-acetyl-N-(5-methyl-isoxazol-3-yl)benzenesulfonamide (Ex-1B, 0.30 g, 1.07 mmol) and 2,4-dimethoxy-5-pyrrolidin-1-ylbenzaldehyde (Ex-38B, 0.25 g, 1.07 mmol) as a dark red solid, mp 164–165° C. 1H-NMR (300 MHz, CDCl3) δ 8.09–7.93 (m, 4H), 7.35 (d, J=15.3 Hz, 1H), 7.05 (s, 1H), 6.48 (s, 1H), 6.24 (s, 1H), 3.92 (s, 3H), 3.90 (s, 3H), 3.29–3.18 (m, 4H), 2.38 (s, 3H), 2.02–1.91 (s, 4H). MS m/z: 498 (M+), 100%.
Sources & evidence
- ORD record
- ord-4132ac1ffa1a4bd4a7c8224d7fbbb86a
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07173129B2
Reaction notes
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