Methanesulfonamide → 5-chloro-4-((2-cyanoadamantan-2-yl)methoxy)-2-fluoro-N-((2-methoxyethyl)sulfonyl)benzamide
Reaction equation
CS(N)(=O)=O.[CH3:6][O:7][CH2:8][CH2:9][S:10]([NH2:13])(=[O:12])=[O:11].C(C1(COC2C(C3CC3)=CC(C(O)=O)=C(F)C=2)C2CC3CC(CC1C3)C2)#N.[Cl:41][C:42]1[C:43]([O:52][CH2:53][C:54]2([C:64]#[N:65])[CH:61]3[CH2:62][CH:57]4[CH2:58][CH:59]([CH2:63][CH:55]2[CH2:56]4)[CH2:60]3)=[CH:44][C:45]([F:51])=[C:46]([CH:50]=1)[C:47](O)=[O:48]>>[Cl:41][C:42]1[C:43]([O:52][CH2:53][C:54]2([C:64]#[N:65])[CH:55]3[CH2:56][CH:57]4[CH2:58][CH:59]([CH2:60][CH:61]2[CH2:62]4)[CH2:63]3)=[CH:44][C:45]([F:51])=[C:46]([CH:50]=1)[C:47]([NH:13][S:10]([CH2:9][CH2:8][O:7][CH3:6])(=[O:12])=[O:11])=[O:48]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 2-methoxyethanesulfonamide 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 a 5:1 mixture of hexanes in diethyl ether (10 mL) as a colorless powder (0.094 g, 63%): 1H NMR (300 MHz, DMSO-d6) δ 12.13 (br s, 1H), 7.70 (d, J=7.4 Hz, 1H), 7.40 (d, J=12.2 Hz, 1H), 4.54 (s, 2H), 3.70 (s, 4H), 3.18 (s, 3H), 2.15-2.07 (m, 4H), 1.97-1.78 (m, 6H), 1.70-1.60 (m, 4H); MS (ES−) m/z 483.2, 485.2 (M−1).
Sources & evidence
- ORD record
- ord-a1c109ce248549b09a84363eaf47887f
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952169B2
Reaction notes
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