Tricyclo(3.3.1.1'3,7)dec-1-ylmethanol → HCID 91809366, compound

HRID 1849577Notes

Reaction equation

HRID 1849577 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]12[C@H:56]([OH:57])[CH2:55][C@@H:51]([C:52]1([CH3:54])[CH3:53])[CH2:50][CH2:49]2>>[Cl:17][C:18]1[C:19]([O:57][C@@H:56]2[CH2:55][C@H:51]3[C:52]([CH3:54])([CH3:53])[C@:48]2([CH3:47])[CH2:49][CH2:50]3)=[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 1201518[(1S)-endo]-(-)-BorneolHCID 580424175-chloro-2,4-difluoro-N-(methylsulfonyl)benzamideHCID 867028365-chloro-N-(N,N-dimethylsulfamoyl)-2,4-difluorobenzamide

Product 1

HCID 91809366HCID 91809366, 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-(N,N-dimethylsulfamoyl)-2,4-difluorobenzamide and adamantan-1-ylmethanol with [(1S)-endo]-(−)-borneol, the title compound was obtained as a colorless solid (0.17 g, 34%): 1H NMR (300 MHz, CDCl3) δ 8.64 (s, 1H), 8.20-8.00 (m, 1H), 6.67-6.43 (m, 1H), 4.47-4.25 (m, 1H), 3.03 (s, 6H), 2.55-2.20 (m, 2H), 1.92-1.69 (m, 2H), 1.51-1.19 (m, 2H), 1.19-0.74 (m, 10H); MS (ES−) m/z 431.2 (M−1), 433.2 (M−1).

Sources & evidence

ORD record
ord-f9c58368de51485db34957a00f93c3b2
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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