Tricyclo(3.3.1.1'3,7)dec-1-ylmethanol → 5-chloro-4-(((1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-yl)methoxy)-N-(N,N-dimethylsulfamoyl)-2-fluorobenzamide

HRID 1849530Notes

Reaction equation

HRID 1849530 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.[CH3:47][C:48]1([CH3:57])[C@H:53]2[CH2:54][C@@H:49]1[CH2:50][CH2:51][C@H:52]2[CH2:55][OH:56]>>[Cl:17][C:18]1[C:19]([O:56][CH2:55][C@@H:52]2[CH2:51][CH2:50][C@H:49]3[CH2:54][C@@H:53]2[C:48]3([CH3:57])[CH3:47])=[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

HCID 64556Tricyclo(3.3.1.1'3,7)dec-1-ylmethanolHCID 11084102(-)-cis-MyrtanolHCID 580424175-chloro-2,4-difluoro-N-(methylsulfonyl)benzamideHCID 867028365-chloro-N-(N,N-dimethylsulfamoyl)-2,4-difluorobenzamide

Product 1

HCID 867028745-chloro-4-(((1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-yl)methoxy)-N-(N,N-dimethylsulfamoyl)-2-fluorobenzamide

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 ((1S,2R,5S)-6,6-dimethylbicyclo[3.1.1]-heptan-2-yl)methanol, the title compound was obtained as a colorless solid (0.12 g, 29%): 1H NMR (300 MHz, DMSO-d6) 11.76 (s, 1H), 7.72 (d, J=6.1 Hz, 1H), 7.26 (d, J=13.2 Hz, 1H), 4.12-4.05 (m, 2H), 2.87 (s, 6H), 2.38-2.37 (m, 1H), 2.13-1.90 (m, 6H), 1.56 (m, 1H), 1.18 (s, 3H), 1.00-0.92 (m, 4H); MS (ES−) m/z 431.1, 433.1 (M−1).

Sources & evidence

ORD record
ord-4be7bac293a942658ddf8c255dc35801
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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