4-((adamantan-2-yloxy)methyl)-5-chloro-2-fluoro-N-(methylsulfonyl)benzamide → HCID 86703516, compound

HRID 1849653Notes

Reaction equation

HRID 1849653 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:45][CH2:46][CH:47]2[CH2:54][CH2:53][C:50]3([CH2:52][CH2:51]3)[CH2:49][CH2:48]2)=[CH:31][C:32]([F:44])=[C:33]([CH:43]=1)[C:34]([NH:36][S:37]([CH:40]1[CH2:42][CH2:41]1)(=[O:39])=[O:38])=[O:35]>>[CH:10]1([C:29]2[C:30]([O:45][CH2:46][CH:47]3[CH2:54][CH2:53][C:50]4([CH2:52][CH2:51]4)[CH2:49][CH2:48]3)=[CH:31][C:32]([F:44])=[C:33]([CH:43]=2)[C:34]([NH:36][S:37]([CH:40]2[CH2:41][CH2:42]2)(=[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 86703515HCID 86703515, compound

Product 1

HCID 86703516HCID 86703516, 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 5-chloro-N-(cyclopropylsulfonyl)-2-fluoro-4-(spiro[2.5]octan-6-ylmethoxy)benzamide, the title compound was obtained as a colorless solid (0.024 g, 18%): 1H NMR (300 MHz, CDCl3) δ8.76-8.62 (m, 1H), 7.63-7.54 (m, 1H), 6.63-6.53 (m, 1H), 3.96-3.78 (m, 2H), 3.20-3.02 (m, 1H), 2.12-1.72 (m, 6H), 1.50-1.41 (m, 2H), 1.40-1.22 (m, 2H), 1.20-1.10 (m, 2H), 1.02-0.88 (m, 4H), 0.72-0.61 (m, 2H), 0.38-0.15 (m, 4H); MS (ES+) m/z 422.2 (M+1).

Sources & evidence

ORD record
ord-e661dada038a4240aaa7b346abedfc4e
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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