4-((adamantan-2-yloxy)methyl)-5-chloro-2-fluoro-N-(methylsulfonyl)benzamide → HCID 178505173, compound

HRID 1849675Notes

Reaction equation

HRID 1849675 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][C@H:45]2[CH2:50][CH2:49][C@@H:48]([C:51]([F:54])([F:53])[F:52])[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:10]1([C:29]2[C:30]([O:43][CH2:44][C@H:45]3[CH2:50][CH2:49][C@@H:48]([C:51]([F:54])([F:53])[F:52])[CH2:47][CH2:46]3)=[CH:31][C:32]([F:42])=[C:33]([CH:41]=2)[C:34]([NH:36][S:37]([CH3:40])(=[O:39])=[O:38])=[O:35])[CH2:1][CH2:2]1

Participants

3

Reactant 2

HCID 867028574-((adamantan-2-yloxy)methyl)-5-chloro-2-fluoro-N-(methylsulfonyl)benzamideHCID 178505176HCID 178505176, compound

Product 1

HCID 178505173HCID 178505173, compound

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 cis-5-chloro-2-fluoro-N-(methylsulfonyl)-4-((4-(trifluoromethyl)cyclohexyl)methoxy)benzamide, the title compound was obtained as colorless solid (0.12 g, 24%): 1H NMR (300 MHz, DMSO-d6) δ 11.89 (s, 1H), 7.13 (d, J=8.3 Hz, 1H), 7.04 (d, J=13.1 Hz, 1H), 4.06 (d, J=7.1 Hz, 2H), 3.34 (s, 3H), 2.36-2.28 (m, 1H), 2.13-1.97 (m, 2H), 1.74-1.56 (m, 8H), 0.91-0.85 (m, 2H), 0.70-0.65 (m, 2H); MS (ES+) m/z 438.1 (M+1); MS (ES−) m/z 436.2 (M−1).

Sources & evidence

ORD record
ord-42faa1bf02ea449a85685c69f0cd1c1a
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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