HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanesulfonamide → 4-(adamantan-1-ylmethoxy)-5-chloro-2-fluoro-N-((3-fluoroazetidin-1-yl)-sulfonyl)benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanesulfonamide | HCID 72879 | — |
| Reactant | 3-Fluoroazetidine-1-sulfonamide | HCID 70347983 | — |
| Reactant | 4-(Adamantan-1-ylmethoxy)-5-chloro-2-fluorobenzoic acid | HCID 86702859 | — |
| Reactant | 4-(Adamantan-1-ylmethoxy)-5-cyclopropyl-2-fluorobenzoic acid | HCID 86702861 | — |
| Product | 4-(adamantan-1-ylmethoxy)-5-chloro-2-fluoro-N-((3-fluoroazetidin-1-yl)-sulfonyl)benzamide | HCID 86702899 | — |
Reaction Steps
Following the procedure as described in Example 50 step 5 and making variations as required to replace 4-(adamantan-1-ylmethoxy)-5-cyclopropyl-2-fluorobenzoic acid with 4-(adamantan-1-ylmethoxy)-5-chloro-2-fluorobenzoic acid and methanesulfonamide with 3-fluoroazetidine-1-sulfonamide, the title compound was obtained as colorless solid (0.15 g, 52%): 1H NMR (300 MHz, DMSO-d6) δ 12.02 (s, 1H), 7.77 (d, J=7.5 Hz, 1H), 7.25 (d, J=12.4 Hz, 1H), 5.49-5.43 (m, 0.5H), 5.30-5.24 (m, 0.5H), 4.45-4.32 (m, 2H), 4.26-4.13 (m, 2H), 3.73 (s, 2H), 1.99 (br s, 3H), 1.75-1.64 (m, 12H); MS (ES+) m/z 475.1, 477.1 (M+1); MS (ES−) m/z 473.2, 475.2 (M−1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08952169B2 |
| Source dataset | uspto-grants-2015_02 |
| ORD ID | ord-7c4fed68af174f479fc0ab69fcf84dfa |
| Source note | uspto-grants-2015_02 |