Bicyclo(2.2.1)heptane-2-methanol → HCID 86702920, compound

HRID 1849574Notes

Reaction equation

HRID 1849574 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].[C:35]12([CH2:45][OH:46])[CH2:44][CH:39]3[CH2:40][CH:41]([CH2:43]C(C3)C1)[CH2:42]2.C12CC(CC1)CC2CO>>[CH:44]12[CH2:43][CH:41]([CH2:40][CH2:39]1)[CH2:42][CH:35]2[CH2:45][O:46][C:19]1[C:18]([Cl:17])=[CH:32][C:22]([C:23]([NH:25][S:26](=[O:31])(=[O:30])[N:27]([CH3:29])[CH3:28])=[O:24])=[C:21]([F:33])[CH:20]=1

Participants

5

Reactant 4

HCID 21308Bicyclo(2.2.1)heptane-2-methanolHCID 64556Tricyclo(3.3.1.1'3,7)dec-1-ylmethanolHCID 580424175-chloro-2,4-difluoro-N-(methylsulfonyl)benzamideHCID 867028365-chloro-N-(N,N-dimethylsulfamoyl)-2,4-difluorobenzamide

Product 1

HCID 86702920HCID 86702920, 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 2-Norbornanemethanol, the title compound was obtained as a colorless solid (0.17 g, 39%): 1H NMR (300 MHz, CDCl3) δ 8.72-8.54 (m, 1H), 8.12-8.01 (m, 1H), 6.77-6.61 (m, 1H), 4.15-3.67 (m, 2H), 3.01 (s, 6H), 2.49-2.21 (m, 3H), 2.10-1.74 (m, 1H), 1.64-1.05 (m, 6H), 0.83-0.71 (m, 1H); MS (ES−) m/z 403.2 (M−1), 405.2 (M−1).

Sources & evidence

ORD record
ord-44fc0c8a7ff24f44b6c0d6afcf78b841
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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