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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1849672Generated: October 31, 2026

1-Azetidinesulfonamide → 3-((4-((Azetidin-1-ylsulfonyl)carbamoyl)-2-cyclopropyl-5-fluorophenoxy)-methyl)adamantan-1-yl 2,2,2-trifluoroacetate

https://huagongshe.com/reaction/1849672

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1-AzetidinesulfonamideHCID 45080566—
Reactant4-(Adamantan-1-ylmethoxy)-5-cyclopropyl-2-fluorobenzoic acidHCID 86702861—
Reactant3-Cyanoazetidine-1-sulfonamideHCID 86703538—
Reactant5-Cyclopropyl-2-fluoro-4-((3-(2,2,2-trifluoroacetoxy)adamantan-1-yl)methoxy)benzoic acidHCID 86703540—
Product3-((4-((Azetidin-1-ylsulfonyl)carbamoyl)-2-cyclopropyl-5-fluorophenoxy)-methyl)adamantan-1-yl 2,2,2-trifluoroacetateHCID 86703539—

Reaction Steps

Following the procedure as described in Example 230 and making variations as required to replace 4-(adamantan-1-ylmethoxy)-5-cyclopropyl-2-fluorobenzoic acid with 5-cyclopropyl-2-fluoro-4-((3-(2,2,2-trifluoroacetoxy)adamantan-1-yl)methoxy)benzoic acid and to replace 3-cyanoazetidine-1-sulfonamide with azetidine-1-sulfonamide, the title compound was obtained as colorless solid (0.22 g, 47%): 1H NMR (300 MHz, DMSO-d6) δ 11.62 (s, 1H), 7.17 (d, J=8.3 Hz, 1H), 6.95 (d, J=12.9 Hz, 1H), 4.05 (t, J=7.7 Hz, 4H), 3.79 (s, 2H), 2.32 (br s, 2H), 2.19-2.14 (m, 8H), 2.06-2.00 (m, 1H), 1.70-1.59 (m, 6H), 0.95-0.88 (m, 2H), 0.70-0.65 (m, 2H); MS (ES+) m/z 575.1 (M+1); MS (ES−) m/z 573.1 (M−1).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08952169B2
Source datasetuspto-grants-2015_02
ORD IDord-5509d65ac7e14edcb022cd3ed866a528
Source noteuspto-grants-2015_02