Tricyclo(3.3.1.1'3,7)dec-1-ylmethanol → 5-chloro-N-(N,N-dimethylsulfamoyl)-2-fluoro-4-(spiro[5.5]undecan-3-yloxy)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:52]2([CH2:57][CH2:56][CH2:55][CH2:54][CH2:53]2)[CH2:51][CH2:50][CH:49]([OH:58])[CH2:48]1>>[Cl:17][C:18]1[C:19]([O:58][CH:49]2[CH2:48][CH2:47][C:52]3([CH2:53][CH2:54][CH2:55][CH2:56][CH2:57]3)[CH2:51][CH2:50]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[5.5]undecan-3-ol, the title compound was obtained as a colorless solid (0.03 g, 7%). 1H NMR (300 MHz, DMSO-d6) δ 11.73 (s, 1H), 7.72 (d, J=7.6 Hz, 1H), 7.29 (d, J=12.6 Hz, 1H), 4.68-4.60 (m, 1H), 2.86 (s, 6H), 1.84-1.74 (m, 2H), 1.66-1.51 (m, 4H), 1.39-1.21 (m, 12H); MS (ES−) m/z 445.2, 447.2 (M−1).
Sources & evidence
- ORD record
- ord-93cfdb888a0f4b9c8dd4f41142b3f974
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952169B2
Reaction notes
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