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

HRID 1849532Notes

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:31])=[C:22]([CH:30]=1)[C:23]([NH:25][S:26](=[O:29])(=[O:28])[NH2:27])=[O:24].C12(CO)CC3CC(CC(C3)C1)C2.[CH3:45][C:46]1([CH3:55])[C@H:51]2[CH2:52][C@@H:47]1[CH2:48][CH2:49][C@@H:50]2[CH2:53][OH:54]>>[Cl:17][C:18]1[C:19]([O:54][CH2:53][C@H:50]2[CH2:49][CH2:48][C@H:47]3[CH2:52][C@@H:51]2[C:46]3([CH3:55])[CH3:45])=[CH:20][C:21]([F:31])=[C:22]([CH:30]=1)[C:23]([NH:25][S:26](=[O:29])(=[O:28])[NH2:27])=[O:24]

Participants

Reactant 4

HCID 64556Tricyclo(3.3.1.1'3,7)dec-1-ylmethanol

HCID 104476(-)-Myrtanol

HCID 580424175-chloro-2,4-difluoro-N-(methylsulfonyl)benzamide

HCID 867028775-chloro-2,4-difluoro-N-sulfamoylbenzamide

Product 1

HCID 867028765-chloro-4-(((1S,2S,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-yl)-methoxy)-2-fluoro-N-sulfamoylbenzamide

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-2,4-difluoro-N-sulfamoylbenzamide and adamantan-1-ylmethanol with ((1S,2S,5S)-6,6-dimethylbicyclo[3.1.1]heptan-2-yl)methanol, the title compound was obtained as a colorless solid (0.09 g, 15%): 1H NMR (300 MHz, DMSO-d6) δ 11.73 (s, 1H), 7.66 (d, J=7.5 Hz, 1H), 7.58 (s, 2H), 7.22 (d, J=12.4 Hz, 1H), 3.95 (d, J=6.8 Hz, 2H), 2.49-2.38 (m, 1H), 2.10-2.03 (m, 1H), 2.19-1.65 (m, 5H), 1.48-1.34 (m, 2H), 1.22 (s, 3H), 0.86 (s, 3H); MS (ES−) m/z 403.2, 405.2 (M−1).

Sources & evidence

ORD record: ord-43d247f12fd8411686a0ad40f991eb3d
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952169B2

Reaction notes

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