Tricyclo(3.3.1.1'3,7)dec-1-ylmethanol → HCID 86703515, compound

HRID 1849652Notes

Reaction equation

HRID 1849652 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]([CH:29]1[CH2:31][CH2:30]1)(=[O:28])=[O:27])=[O:24].C12(CO)CC3CC(CC(C3)C1)C2.[CH2:47]1[C:49]2([CH2:54][CH2:53][CH:52]([CH2:55][OH:56])[CH2:51][CH2:50]2)[CH2:48]1>>[Cl:17][C:18]1[C:19]([O:56][CH2:55][CH:52]2[CH2:53][CH2:54][C:49]3([CH2:47][CH2:48]3)[CH2:50][CH2:51]2)=[CH:20][C:21]([F:33])=[C:22]([CH:32]=1)[C:23]([NH:25][S:26]([CH:29]1[CH2:31][CH2:30]1)(=[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 86703514HCID 86703514, compound

Product 1

HCID 86703515HCID 86703515, 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-(cyclopropylsulfonyl)-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 (0.165 g, 28%): 1H NMR (300 MHz, CDCl3) δ8.72-8.59 (m, 1H), 8.16-8.07 (m, 1H), 6.76-6.65 (m, 1H), 3.97-3.86 (m, 2H), 3.17-3.05 (m, 1H), 2.03-1.72 (m, 5H), 1.51-1.42 (m, 2H), 1.36-1.11 (m, 4H), 1.00-0.90 (m, 2H), 0.38-0.14 (m, 4H); MS (ES+) m/z 416.2, 418.2 (M+1).

Sources & evidence

ORD record
ord-456b60b4cfdb42ef8a08ef5c25a71224
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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