Methanesulfonamide → 5-Chloro-2-fluoro-N-(methylsulfonyl)-4-((3,5,7-trifluoroadamantan-1-yl)methoxy)benzamide
Reaction equation
C12(COC3C(C4CC4)=CC(C(O)=O)=CN=3)CC3CC(CC(C3)C1)C2.[Cl:25][C:26]1[C:27]([O:36][CH2:37][C:38]23[CH2:48][C:42]4([F:49])[CH2:43][C:44]([F:47])([CH2:46][C:40]([F:50])([CH2:41]4)[CH2:39]2)[CH2:45]3)=[CH:28][C:29]([F:35])=[C:30]([CH:34]=1)[C:31](O)=[O:32].COC[CH2:54][S:55]([NH2:58])(=[O:57])=[O:56].CS(N)(=O)=O>>[Cl:25][C:26]1[C:27]([O:36][CH2:37][C:38]23[CH2:48][C:42]4([F:49])[CH2:43][C:44]([F:47])([CH2:46][C:40]([F:50])([CH2:41]4)[CH2:39]2)[CH2:45]3)=[CH:28][C:29]([F:35])=[C:30]([CH:34]=1)[C:31]([NH:58][S:55]([CH3:54])(=[O:57])=[O:56])=[O:32]Participants
5
Reactant 4
Product 1
Procedure
Following the procedure as described in Example 150 step 5 and making variations as required to replace 6-(adamantan-1-ylmethoxy)-5-cyclopropylnicotinic acid with 5-chloro-2-fluoro-4-((3,5,7-trifluoroadamantan-1-yl)methoxy)benzoic acid and to replace 2-methoxyethanesulfonamide with methyl sulfonamide, the title compound was obtained as a colorless solid (0.035 g, 28%): 1H NMR (300 MHz, DMSO-d6) δ 12.10 (br s, 1H), 7.76 (d, J=7.6 Hz, 1H), 7.20 (d, J=12.28 Hz, 1H), 4.00 (s, 2H), 3.22 (s, 3H), 2.26-2.15 (m, 3H), 2.07-1.97 (m, 3H), 1.82-1.74 (m, 6H); MS (ES−) m/z 468.21, 470.20 (M−1).
Sources & evidence
- ORD record
- ord-13f888257f0340e59f592a9065acd385
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952169B2
Reaction notes
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