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

HRID 1849656Notes

Reaction equation

HRID 1849656 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][CH:41]3[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:54][CH:55]1[CH2:58][N:57]([S:59]([NH2:62])(=[O:61])=[O:60])[CH2:56]1>>[CH:26]1([C:29]2[C:30]([O:39][CH2:40][CH:41]3[CH2:46][CH2:45][C:44]([F:47])([F:48])[CH2:43][CH2:42]3)=[CH:31][C:32]([F:38])=[C:33]([CH:37]=2)[C:34]([NH:62][S:59]([N:57]2[CH2:58][CH:55]([F:54])[CH2:56]2)(=[O:61])=[O:60])=[O:35])[CH2:28][CH2:27]1

Participants

5

Reactant 4

HCID 72879MethanesulfonamideHCID 703479833-Fluoroazetidine-1-sulfonamideHCID 867034505-Cyclopropyl-2-fluoro-4-((1-(trifluoromethyl)-cyclohexyl)methoxy)benzoic acidHCID 867035175-Cyclopropyl-4-((4,4-difluorocyclohexyl)-methoxy)-2-fluorobenzoic acid

Product 1

HCID 867035205-cyclopropyl-4-((4,4-difluorocyclohexyl)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-difluorocyclohexyl)-methoxy)-2-fluorobenzoic acid and to replace methanesulfonamide with 3-fluoroazetidine-1-sulfonamide, the title compound was obtained (0.12 g, 43%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ8.77-8.64 (m, 1H), 7.64-7.55 (m, 1H), 6.62-6.53 (m, 1H), 5.43-5.13 (m, 1H), 4.57-4.31 (m, 4H), 3.94-3.86 (m, 2H), 2.27-2.11 (m, 2H), 2.09-1.68 (m, 6H), 1.61-1.43 (m, 2H), 0.99-0.90 (m, 2H), 0.71-0.63 (m, 2H); MS (ES+) m/z 465.0 (M+1).

Sources & evidence

ORD record
ord-0ddbff1ba93848739e23e8fa9156cf51
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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