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

HRID 1849657Notes

Reaction equation

HRID 1849657 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]([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]([F:47])([F: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 867035175-Cyclopropyl-4-((4,4-difluorocyclohexyl)-methoxy)-2-fluorobenzoic acid

Product 1

HCID 86703521N-(azetidin-1-ylsulfonyl)-5-cyclopropyl-4-((4,4-difluorocyclohexyl)-methoxy)-2-fluorobenzamide

Procedure

Following the procedure as described in preparation of 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 azetidine-1-sulfonamide, the title compound was obtained (0.14 g, 47%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ8.72-8.57 (m, 1H), 7.66-7.54 (m, 1H), 6.64-6.50 (m, 1H), 4.32-4.19 (m, 4H), 3.96-3.83 (m, 2H), 2.35-2.09 (m, 4H), 2.09-1.68 (m, 6H), 1.62-1.41 (m, 2H), 1.04-0.87 (m, 2H), 0.76-0.62 (m, 2H); MS (ES+) m/z 447.0 (M+1).

Workup

  1. customas described in preparation of Example 158 step 5

Sources & evidence

ORD record
ord-5d0c41e511b04b1b87cec48d2994274a
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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