4-((adamantan-2-yloxy)methyl)-5-chloro-2-fluoro-N-(methylsulfonyl)benzamide → 4-((adamantan-1-yloxy)methyl)-N-(azetidin-1-ylsulfonyl)-5-cyclopropyl-2-fluorobenzamide

HRID 1849643Notes

Reaction equation

HRID 1849643 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.[C:28]12([O:38][CH2:39][C:40]3[C:55](Cl)=[CH:54][C:43]([C:44]([NH:46][S:47]([N:50]4[CH2:53][CH2:52][CH2:51]4)(=[O:49])=[O:48])=[O:45])=[C:42]([F:57])[CH:41]=3)[CH2:37][CH:32]3[CH2:33][CH:34]([CH2:36][CH:30]([CH2:31]3)[CH2:29]1)[CH2:35]2>>[C:28]12([O:38][CH2:39][C:40]3[C:55]([CH:10]4[CH2:1][CH2:2]4)=[CH:54][C:43]([C:44]([NH:46][S:47]([N:50]4[CH2:53][CH2:52][CH2:51]4)(=[O:49])=[O:48])=[O:45])=[C:42]([F:57])[CH:41]=3)[CH2:37][CH:32]3[CH2:33][CH:34]([CH2:36][CH:30]([CH2:31]3)[CH2:29]1)[CH2:35]2

Participants

3

Reactant 2

HCID 867028574-((adamantan-2-yloxy)methyl)-5-chloro-2-fluoro-N-(methylsulfonyl)benzamideHCID 867035054-((adamantan-1-yloxy)methyl)-N-(azetidin-1-ylsulfonyl)-5-chloro-2-fluorobenzamide

Product 1

HCID 867035044-((adamantan-1-yloxy)methyl)-N-(azetidin-1-ylsulfonyl)-5-cyclopropyl-2-fluorobenzamide

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 4-((adamantan-1-yloxy)methyl)-N-(azetidin-1-ylsulfonyl)-5-chloro-2-fluorobenzamide, the title compound was obtained as a colorless solid (0.135 g, 83%): 1H NMR (300 MHz, CDCl3) δ8.82-8.68 (m, 1H), 7.76-7.68 (m, 1H), 7.44-7.34 (m, 1H), 4.72 (s, 2H), 4.33-4.18 (m, 4H), 2.35-2.15 (m, 5H), 1.90-1.60 (m, 13H), 1.02-0.89 (m, 2H), 0.73-0.62 (m, 2H); MS (ES+) m/z 463.2 (M+1).

Sources & evidence

ORD record
ord-647908df65654dd580a31cda337739ae
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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