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

HRID 1849638Notes

Reaction equation

HRID 1849638 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]([CH3:48])([CH3:47])[CH2:43][CH2:42]3)=[CH:31][C:32]([F:38])=[C:33]([CH:37]=2)[C:34]([OH:36])=O)[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:36])[C:33]2[CH:37]=[C:29]([CH:26]3[CH2:27][CH2:28]3)[C:30]([O:39][CH2:40][CH:41]3[CH2:46][CH2:45][C:44]([CH3:47])([CH3:48])[CH2:43][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 867034975-Cyclopropyl-4-((4,4-dimethylcyclohexyl)-methoxy)-2-fluorobenzoic acid

Product 1

HCID 86703498N-(azetidin-1-ylsulfonyl)-5-cyclopropyl-4-((4,4-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-((4,4-dimethylcyclohexyl)-methoxy)-2-fluorobenzoic acid and to replace methanesulfonamide with azetidine-1-sulfonamide, the title compound was obtained (0.16 g, 51%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ8.71-8.58 (m, 1H), 7.64-7.56 (m, 1H), 6.64-6.52 (m, 1H), 4.34-4.18 (m, 4H), 3.92-3.80 (m, 2H), 2.36-2.18 (m, 2H), 2.12-1.97 (m, 1H), 1.87-1.66 (m, 3H), 1.51-1.19 (m, 6H), 1.01-0.84 (m, 8H), 0.74-0.62 (m, 2H); MS (ES+) m/z 439.2 (M+1).

Sources & evidence

ORD record
ord-30c7b784903948a18e3bb34ab80fe0d5
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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