Methanesulfonamide → 5-cyclopropyl-4-((4,4-difluoro-1-methylcyclohexyl)methoxy)-2-fluoro-N-((3-fluoroazetidin-1-yl)sulfonyl)benzamide

HRID 1849622Notes

Reaction equation

HRID 1849622 reaction equation
C1(C2C(OCC3(C(F)(F)F)CCCCC3)=CC(F)=C(C=2)C(O)=O)CC1.[CH:26]1([C:29]2[C:30]([O:39][CH2:40][C:41]3([CH3:49])[CH2:46][CH2:45][C:44]([F:48])([F:47])[CH2:43][CH2:42]3)=[CH:31][C:32]([F:38])=[C:33]([CH:37]=2)[C:34](O)=[O:35])[CH2:28][CH2:27]1.CS(N)(=O)=O.[F:55][CH:56]1[CH2:59][N:58]([S:60]([NH2:63])(=[O:62])=[O:61])[CH2:57]1>>[CH:26]1([C:29]2[C:30]([O:39][CH2:40][C:41]3([CH3:49])[CH2:42][CH2:43][C:44]([F:47])([F:48])[CH2:45][CH2:46]3)=[CH:31][C:32]([F:38])=[C:33]([CH:37]=2)[C:34]([NH:63][S:60]([N:58]2[CH2:59][CH:56]([F:55])[CH2:57]2)(=[O:62])=[O:61])=[O:35])[CH2:27][CH2:28]1

Participants

5

Reactant 4

HCID 72879MethanesulfonamideHCID 703479833-Fluoroazetidine-1-sulfonamideHCID 867034505-Cyclopropyl-2-fluoro-4-((1-(trifluoromethyl)-cyclohexyl)methoxy)benzoic acidHCID 867034725-Cyclopropyl-4-((4,4-difluoro-1-methylcyclohexyl)methoxy)-2-fluorobenzoic acid

Product 1

HCID 867034775-cyclopropyl-4-((4,4-difluoro-1-methylcyclohexyl)methoxy)-2-fluoro-N-((3-fluoroazetidin-1-yl)sulfonyl)benzamide

Procedure

Following the procedure as described in Example 158 step 5, and making variations as required to replace 5-cyclopropyl-2-fluoro-4-((1-(trifluoromethyl)cyclohexyl)methoxy)-benzoic acid with 5-cyclopropyl-4-((4,4-difluoro-1-methylcyclohexyl)methoxy)-2-fluorobenzoic acid and to replace methanesulfonamide with 3-fluoroazetidine-1-sulfonamide, the title compound was obtained (0.06 g, 20%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ8.81-8.63 (m, 1H), 7.70-7.58 (m, 1H), 6.66-6.50 (m, 1H), 5.45-5.13 (m, 1H), 4.59-4.29 (m, 4H), 3.77 (s, 2H), 2.09-1.74 (m, 7H), 1.69-1.60 (m, 2H), 1.17 (s, 3H), 1.01-0.89 (m, 2H), 0.71-0.60 (m, 2H); MS (ES+) m/z 479.1 (M+1).

Sources & evidence

ORD record
ord-92e2e75fd19c4db683d86b62d46e46df
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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