Tricyclo(3.3.1.1'3,7)dec-1-ylmethanol → 5-chloro-N-(N,N-dimethylsulfamoyl)-2-fluoro-4-(spiro[3.5]nonan-7-ylmethoxy)-benzamide
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.[CH2:47]1[C:50]2([CH2:55][CH2:54][CH:53]([CH2:56][OH:57])[CH2:52][CH2:51]2)[CH2:49][CH2:48]1>>[Cl:17][C:18]1[C:19]([O:57][CH2:56][CH:53]2[CH2:52][CH2:51][C:50]3([CH2:49][CH2:48][CH2:47]3)[CH2:55][CH2:54]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 spiro[3.5]nonan-7-ylmethanol, the title compound was obtained as a colorless solid (0.26 g, 47%): 1H NMR (300 MHz, CDCl3) δ 8.61 (br s, 1H), 8.05 (d, J=8.4 Hz, 1H), 6.65 (d, J=13.5 Hz, 1H), 3.82 (d, J=6.3 Hz, 2H), 3.01 (s, 6H), 1.89-1.65 (m, 11H), 1.35-1.04 (m, 4H); MS (ES−) m/z: 431.2, 433.2 (M−1).
Sources & evidence
- ORD record
- ord-430d4fd7dba84416b8a13a7d640a5667
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08933236B2
Reaction notes
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