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

HRID 1849620Notes

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]([OH:36])=O)[CH2:28][CH2:27]1.CS(N)(=O)=O.[N:55]1([S:59]([NH2:62])(=[O:61])=[O:60])[CH2:58][CH2:57][CH2:56]1>>[N:55]1([S:59]([NH:62][C:34](=[O:36])[C:33]2[CH:37]=[C:29]([CH:26]3[CH2:28][CH2:27]3)[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]=2[F:38])(=[O:61])=[O:60])[CH2:58][CH2:57][CH2:56]1

Participants

Reactant 4

HCID 72879Methanesulfonamide

HCID 450805661-Azetidinesulfonamide

HCID 867034505-Cyclopropyl-2-fluoro-4-((1-(trifluoromethyl)-cyclohexyl)methoxy)benzoic acid

HCID 867034725-Cyclopropyl-4-((4,4-difluoro-1-methylcyclohexyl)methoxy)-2-fluorobenzoic acid

Product 1

HCID 86703475N-(azetidin-1-ylsulfonyl)-5-cyclopropyl-4-((4,4-difluoro-1-methylcyclohexyl)-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-difluoro-1-methylcyclohexyl)methoxy)-2-fluorobenzoic acid and to replace methanesulfonamide with azetidine-1-sulfonamide, the title compound was obtained (0.17 g, 56%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ 8.72-8.59 (m, 1H), 7.69-7.61 (m, 1H), 6.64-6.52 (m, 1H), 4.31-4.19 (m, 4H), 3.76 (s, 2H), 2.35-2.20 (m, 2H), 2.08-1.73 (m, 7H), 1.69-1.58 (m, 2H), 1.17 (s, 3H), 0.99-0.89 (m, 2H), 0.71-0.61 (m, 2H); MS (ES+) m/z 461.1 (M+1).

Sources & evidence

ORD record: ord-da71a1edaebe4dbd958e0fd4e9ea4d33
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952169B2

Reaction notes

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