Methanesulfonamide → N-(azetidin-1-ylsulfonyl)-5-cyclopropyl-4-((3,3-dimethylcyclohexyl)-methoxy)-2-fluorobenzamide

HRID 1849642Notes

Reaction equation

HRID 1849642 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][CH2:44][C:43]([CH3:48])([CH3:47])[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.[N:54]1([S:58]([NH2:61])(=[O:60])=[O:59])[CH2:57][CH2:56][CH2:55]1>>[N:54]1([S:58]([NH:61][C:34](=[O:35])[C:33]2[CH:37]=[C:29]([CH:26]3[CH2:28][CH2:27]3)[C:30]([O:39][CH2:40][CH:41]3[CH2:46][CH2:45][CH2:44][C:43]([CH3:48])([CH3:47])[CH2:42]3)=[CH:31][C:32]=2[F:38])(=[O:60])=[O:59])[CH2:57][CH2:56][CH2:55]1

Participants

5

Reactant 4

HCID 72879MethanesulfonamideHCID 450805661-AzetidinesulfonamideHCID 867034505-Cyclopropyl-2-fluoro-4-((1-(trifluoromethyl)-cyclohexyl)methoxy)benzoic acidHCID 867035025-Cyclopropyl-4-((3,3-dimethylcyclohexyl)-methoxy)-2-fluorobenzoic acid

Product 1

HCID 86703503N-(azetidin-1-ylsulfonyl)-5-cyclopropyl-4-((3,3-dimethylcyclohexyl)-methoxy)-2-fluorobenzamide

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-((3,3-dimethylcyclohexyl)-methoxy)-2-fluorobenzoic acid and to replace methanesulfonamide with azetidine-1-sulfonamide, the title compound was obtained (0.12 g, 41%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ8.72-8.59 (m, 1H), 7.63-7.55 (m, 1H), 6.61-6.51 (m, 1H), 4.34-4.16 (m, 4H), 3.86-3.70 (m, 2H), 2.34-2.20 (m, 2H), 2.13-2.00 (m, 2H), 1.97-1.86 (m, 1H), 1.70-1.38 (m, 4H), 1.20-0.90 (m, 11H), 0.72-0.63 (m, 2H); MS (ES+) m/z 439.2 (M+1).

Sources & evidence

ORD record
ord-2e259939db07408293da14fb91d8b5aa
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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