2-Cyclohexylethanol → 5-chloro-4-(2-cyclohexylethoxy)-N-(N,N-dimethyl-sulfamoyl)-2-fluorobenzamide
Reaction equation
ClC1C(F)=CC(F)=C(C=1)C(NS(C)(=O)=O)=O.[Cl:17][C:18]1[C:19](F)=[CH:20][C:21]([F:33])=[C:22]([CH:32]=1)[C:23]([NH:25][S:26](=[O:31])(=[O:30])[N:27]([CH3:29])[CH3:28])=[O:24].C12(CO)CC3CC(CC(C3)C1)C2.[CH:47]1([CH2:53][CH2:54][OH:55])[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]1>>[Cl:17][C:18]1[C:19]([O:55][CH2:54][CH2:53][CH:47]2[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]2)=[CH:20][C:21]([F:33])=[C:22]([CH:32]=1)[C:23]([NH:25][S:26](=[O:31])(=[O:30])[N:27]([CH3:29])[CH3:28])=[O:24]Participants
5
Reactant 4
Product 1
Procedure
Following the procedure as described in Example 8 and making variations as required to replace 5-chloro-2,4-difluoro-N-(methylsulfonyl)benzamide with 5-chloro-N—(N,N-dimethylsulfamoyl)-2,4-difluorobenzamide and adamantan-1-ylmethanol with 2-cyclohexylethanol, the title compound was obtained as a colorless solid (0.09 g, 22%): 1H NMR (300 MHz, DMSO-d6) δ 11.77 (s, 1H), 7.72 (d, J=7.5 Hz, 1H), 7.26 (d, J=12.4 Hz, 1H), 4.17 (t, J=6.6 Hz, 2H), 2.87 (s, 6H), 1.76-1.60 (m, 7H), 1.54-1.42 (m, 1H), 1.28-1.11 (m, 3H), 1.02-0.90 (m, 2H); MS (ES−) m/z 405.1, 407.1 (M−1).
Sources & evidence
- ORD record
- ord-bddc5da2141340f78709c923f5802edf
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08933236B2
Reaction notes
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