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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1849761Generated: November 2, 2026

Methanesulfonamide → 4-(adamantan-1-ylmethoxy)-2-fluoro-5-(trans-2-(methoxymethyl)-cyclopropyl)-N-(methylsulfonyl)benzamide

https://huagongshe.com/reaction/1849761

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanesulfonamideHCID 72879—
Reactant1-AzetidinesulfonamideHCID 45080566—
Reactant4-(Adamantan-1-ylmethoxy)-2-fluoro-5-iodobenzoic acidHCID 86703604—
Reactant4-(Adamantan-1-ylmethoxy)-2-fluoro-5-(trans-2-(methoxymethyl)cyclopropyl)benzoic acidHCID 86703643—
Product4-(adamantan-1-ylmethoxy)-2-fluoro-5-(trans-2-(methoxymethyl)-cyclopropyl)-N-(methylsulfonyl)benzamideHCID 86703644—

Reaction Steps

Following the procedure as described in Example 299 Step 2 and making variations as required to replace 4-(adamantan-1-ylmethoxy)-2-fluoro-5-iodobenzoic acid with 4-(adamantan-1-ylmethoxy)-2-fluoro-5-(trans-2-(methoxymethyl)cyclopropyl)benzoic acid and to replace azetidine-1-sulfonamide with methanesulfonamide, the title compound was obtained as a colorless solid (0.0678 g, quant.): 1H NMR (300 MHz, DMSO-d6) δ 11.89 (br s, 1H), 7.18 (d, J=8.3 Hz, 1H), 6.93 (d, J=13.1 Hz, 1H), 3.66 (d, J=9.4 Hz, 1H), 3.61 (d, J=9.5 Hz, 1H), 3.46-3.35 (m, 2H), 3.34 (s, 3H), 3.25 (s, 3H), 2.04-1.89 (m, 4H), 1.78-1.61 (m, 12H), 1.34-1.22 (m, 1H), 1.06-0.97 (m, 1H), 0.90-0.81 (m, 1H); MS (ES−) m/z 464.2 (M−1).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08952169B2
Source datasetuspto-grants-2015_02
ORD IDord-08f24091e5024bd19b53df06e8632778
Source noteuspto-grants-2015_02