Tricyclo(3.3.1.1'3,7)dec-1-ylmethanol → HCID 86703554, compound

HRID 1849684Notes

Reaction equation

HRID 1849684 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:32])=[C:22]([CH:31]=1)[C:23]([NH:25][S:26]([CH2:29][CH3:30])(=[O:28])=[O:27])=[O:24].C12(CO)CC3CC(CC(C3)C1)C2.[CH2:46]1[C:48]2([CH2:53][CH2:52][CH:51]([CH2:54][OH:55])[CH2:50][CH2:49]2)[CH2:47]1>>[Cl:17][C:18]1[C:19]([O:55][CH2:54][CH:51]2[CH2:52][CH2:53][C:48]3([CH2:46][CH2:47]3)[CH2:49][CH2:50]2)=[CH:20][C:21]([F:32])=[C:22]([CH:31]=1)[C:23]([NH:25][S:26]([CH2:29][CH3:30])(=[O:28])=[O:27])=[O:24]

Participants

5

Reactant 4

HCID 64556Tricyclo(3.3.1.1'3,7)dec-1-ylmethanolHCID 53487089(Spiro(2.5)octan-6-yl)methanolHCID 580424175-chloro-2,4-difluoro-N-(methylsulfonyl)benzamideHCID 86703555HCID 86703555, compound

Product 1

HCID 86703554HCID 86703554, compound

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-(ethylsulfonyl)-2,4-difluorobenzamide and to replace adamantan-1-ylmethanol with spiro[2.5]octan-6-ylmethanol, the title compound was obtained as a colorless solid (0.378 g, 46%): 1H NMR (300 MHz, CDCl3) δ8.59-8.47 (m, 1H), 8.13-8.05 (m, 1H), 6.75-6.66 (m, 1H), 3.97-3.86 (m, 2H), 3.66-3.55 (m, 2H), 2.02-1.72 (m, 5H), 1.48-1.40 (m, 3H), 1.35-1.22 (m, 2H), 1.01-0.89 (m, 2H), 0.37-0.15 (m, 4H); MS (ES+) m/z 404.1, 406.1 (M+1).

Sources & evidence

ORD record
ord-59745565a06c47a2962c722089450000
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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