4-((adamantan-2-yloxy)methyl)-5-chloro-2-fluoro-N-(methylsulfonyl)benzamide → 4-(cyclohexylmethoxy)-5-cyclopropyl-2-fluoro-N-(methylsulfonyl)benzamide

HRID 1849626Notes

Reaction equation

HRID 1849626 reaction equation
[CH:1]12[CH2:10]C3CC(CC(C3)[CH:2]1OCC1C(Cl)=CC(C(NS(C)(=O)=O)=O)=C(F)C=1)C2.Cl[C:29]1[C:30]([O:43][CH2:44][CH:45]2[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]2)=[CH:31][C:32]([F:42])=[C:33]([CH:41]=1)[C:34]([NH:36][S:37]([CH3:40])(=[O:39])=[O:38])=[O:35]>>[CH:45]1([CH2:44][O:43][C:30]2[C:29]([CH:10]3[CH2:1][CH2:2]3)=[CH:41][C:33]([C:34]([NH:36][S:37]([CH3:40])(=[O:39])=[O:38])=[O:35])=[C:32]([F:42])[CH:31]=2)[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]1

Participants

3

Reactant 2

HCID 867028574-((adamantan-2-yloxy)methyl)-5-chloro-2-fluoro-N-(methylsulfonyl)benzamideHCID 867034835-chloro-4-(cyclohexylmethoxy)-2-fluoro-N-(methylsulfonyl)benzamide

Product 1

HCID 867034824-(cyclohexylmethoxy)-5-cyclopropyl-2-fluoro-N-(methylsulfonyl)benzamide

Procedure

Following the procedure as described in Example 49 and making variations as required to replace 4-((adamantan-2-yloxy)methyl)-5-chloro-2-fluoro-N-(methylsulfonyl)benzamide with 5-chloro-4-(cyclohexylmethoxy)-2-fluoro-N-(methylsulfonyl)benzamide, the title compound was obtained as a colorless solid (0.19 g, 14%): 1H NMR (300 MHz, CDCl3) δ8.77-8.66 (m, 1H), 7.61-7.52 (m, 1H), 6.62-6.52 (m, 1H), 3.86-3.78 (m, 2H), 3.41 (s, 3H), 2.12-1.99 (m, 1H), 1.95-1.66 (m, 6H), 1.40-1.03 (m, 5H), 0.99-0.89 (m, 2H), 0.69-0.61 (m, 2H); MS (ES−) m/z 368.3 (M−1).

Sources & evidence

ORD record
ord-fa6fab177ecd487e8b6a0d0e7e753efb
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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