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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1849648Generated: November 1, 2026

Methanesulfonamide → 4-(adamantan-2-ylmethoxy)-N-(azetidin-1-ylsulfonyl)-5-cyclopropyl-2-fluorobenzamide

https://huagongshe.com/reaction/1849648

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanesulfonamideHCID 72879—
Reactant1-AzetidinesulfonamideHCID 45080566—
Reactant5-Cyclopropyl-2-fluoro-4-((1-(trifluoromethyl)-cyclohexyl)methoxy)benzoic acidHCID 86703450—
Reactant4-(Adamantan-2-ylmethoxy)-5-cyclopropyl-2-fluorobenzoic acidHCID 86703509—
Product4-(adamantan-2-ylmethoxy)-N-(azetidin-1-ylsulfonyl)-5-cyclopropyl-2-fluorobenzamideHCID 86703511—

Reaction Steps

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 4-(adamantan-2-ylmethoxy)-5-cyclopropyl-2-fluorobenzoic acid and to replace methanesulfonamide with azetidine-1-sulfonamide, the title compound was obtained (0.07 g, 26%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ8.72-8.62 (m, 1H), 7.60-7.54 (m, 1H), 6.67-6.59 (m, 1H), 4.31-4.20 (m, 4H), 4.14-4.07 (m, 2H), 2.36-2.20 (m, 3H), 2.08-1.75 (m, 13H), 1.70-1.60 (m, 2H), 0.97-0.89 (m, 2H), 0.71-0.63 (m, 2H); MS (ES−) m/z 461.3 (M−1).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08952169B2
Source datasetuspto-grants-2015_02
ORD IDord-22d86365d084481198fad523496a3cb7
Source noteuspto-grants-2015_02