Methanesulfonamide → 4-((1-cyanocyclohexyl)methoxy)-5-cyclopropyl-N-(cyclopropylsulfonyl)-2-fluorobenzamide
Reaction equation
[C:1]([C:3]1([CH2:13][O:14][C:15]2[C:23]([CH:24]3[CH2:26][CH2:25]3)=[CH:22][C:18]([C:19]([OH:21])=O)=[C:17]([F:27])[CH:16]=2)[CH:10]2[CH2:11][CH:6]3CC(C[CH:4]1[CH2:5]3)C2)#[N:2].C(C1(COC2C(C3CC3)=CC(C(O)=O)=C(F)C=2)CCCCC1)#N.CS(N)(=O)=O.[CH:56]1([S:59]([NH2:62])(=[O:61])=[O:60])[CH2:58][CH2:57]1>>[C:1]([C:3]1([CH2:13][O:14][C:15]2[C:23]([CH:24]3[CH2:26][CH2:25]3)=[CH:22][C:18]([C:19]([NH:62][S:59]([CH:56]3[CH2:58][CH2:57]3)(=[O:61])=[O:60])=[O:21])=[C:17]([F:27])[CH:16]=2)[CH2:10][CH2:11][CH2:6][CH2:5][CH2:4]1)#[N:2]Participants
Reactant 4
Product 1
Procedure
Following the procedure as described in Example 332 Step 7 and making non-critical variations to replace 4-((2-cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acid with 4-((1-cyanocyclohexyl)methoxy)-5-cyclopropyl-2-fluorobenzoic acid and making variations as required to replace methanesulfonamide with cyclopropanesulfonamide, the title compound was obtained as a colorless solid (0.092 g, 66% yield): 1H NMR (300 MHz, DMSO-d6) δ 11.86 (br s, 1H), 7.13 (d, J=8.2 Hz, 1H), 6.99 (d, J=12.8 Hz, 1H), 4.15 (s, 2H), 3.08-3.00 (m, 1H), 2.03-1.95 (m, 3H), 1.73-1.66 (m, 3H), 1.51-1.38 (m, 4H), 1.23-1.15 (m, 1H), 1.09-1.05 (m, 4H), 0.91-0.85 (m, 2H), 0.69-0.64 (m, 2H); 19F NMR (282 MHz, DMSO-d6) δ −112.3 (s, 1F); MS (ES−) m/z 419.2 (M−1).
Sources & evidence
- ORD record
- ord-87074592b8e44eb19a03b088749bfa05
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952169B2
Reaction notes
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