Methanesulfonamide → 5-chloro-4-((2-cyanoadamantan-2-yl)methoxy)-2-fluoro-N-(N-methylsulfamoyl)benzamide
Reaction equation
CS(N)(=O)=O.[CH3:6][NH:7][S:8]([NH2:11])(=[O:10])=[O:9].C(C1(COC2C(C3CC3)=CC(C(O)=O)=C(F)C=2)C2CC3CC(CC1C3)C2)#N.[Cl:39][C:40]1[C:41]([O:50][CH2:51][C:52]2([C:62]#[N:63])[CH:59]3[CH2:60][CH:55]4[CH2:56][CH:57]([CH2:61][CH:53]2[CH2:54]4)[CH2:58]3)=[CH:42][C:43]([F:49])=[C:44]([CH:48]=1)[C:45]([OH:47])=O>>[Cl:39][C:40]1[C:41]([O:50][CH2:51][C:52]2([C:62]#[N:63])[CH:59]3[CH2:58][CH:57]4[CH2:56][CH:55]([CH2:54][CH:53]2[CH2:61]4)[CH2:60]3)=[CH:42][C:43]([F:49])=[C:44]([CH:48]=1)[C:45]([NH:11][S:8](=[O:10])(=[O:9])[NH:7][CH3:6])=[O:47]Participants
5
Reactant 4
Product 1
Procedure
Following the procedure as described in Example 332 Step 7 and making non-critical variations to replace methanesulfonamide with methyl sulfamide and to replace 4-((2-cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acid with 5-chloro-4-((2-cyanoadamantan-2-yl)methoxy)-2-fluorobenzoic acid, the title compound was obtained following trituration with diethyl ether (10 mL) as a colorless powder (0.073 g, 52%): 1H NMR (300 MHz, DMSO-d6) δ 11.72 (s, 1H), 7.73-7.66 (m, 2H), 7.34 (d, J=12.2 Hz, 1H), 4.54 (s, 2H), 2.53 (d, J=4.6 Hz, 3H), 2.15-2.07 (m, 4H), 1.97-1.78 (m, 6H), 1.70-1.60 (m, 4H); MS (ES−) m/z 454.1, 456.1 (M−1).
Sources & evidence
- ORD record
- ord-c31b85ed480b402fa050ae8705138a4c
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952169B2
Reaction notes
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