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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1849809Generated: October 30, 2026

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

https://huagongshe.com/reaction/1849809

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanesulfonamideHCID 72879—
Reactant1-AzetidinesulfonamideHCID 45080566—
Reactant4-((2-Cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acidHCID 86703655—
Reactant5-Cyclopropyl-4-((3,3-dimethylcyclohexyl)oxy)-2-fluorobenzoic acidHCID 86703693—
ProductN-(azetidin-1-ylsulfonyl)-5-cyclopropyl-4-((3,3-dimethylcyclohexyl)oxy)-2-fluorobenzamideHCID 86703694—

Reaction Steps

Following the procedure as described in Example 332 Step 7 and making non-critical variations to replace methane sulfonamide with azetidine-1-sulfonamide and to replace 4-((2-cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acid with 5-cyclopropyl-4-((3,3-dimethylcyclohexyl)oxy)-2-fluorobenzoic acid, the title compound was obtained as a white solid (0.035 g, 15%): 1H NMR (300 MHz, DMSO-d6) δ11.58 (s, 1H), 7.11 (d, J=8.5 Hz, 1H), 7.03 (d, J=13.3 Hz, 1H), 4.67-4.58 (m, 1H), 4.04 (t, J=7.7 Hz, 4H), 2.21-2.11 (m, 2H), 2.06-1.96 (m, 2H), 1.76-1.70 (m, 1H), 1.65-1.53 (m, 2H), 1.38-1.14 (m, 4H), 0.98 (s, 3H), 0.97 (s, 3H), 0.90-0.84 (m, 2H), 0.69-0.64 (m, 2H); MS (ES+) m/z 425.1 (M+1).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08952169B2
Source datasetuspto-grants-2015_02
ORD IDord-fe50f4a87eda4eb39ef65331cc4c2575
Source noteuspto-grants-2015_02