HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanesulfonamide → 5-cyclopropyl-N-(cyclopropylsulfonyl)-4-(((1RS,6SR)-7,7-difluorobicyclo[4.1.0]heptan-1-yl)methoxy)-2-fluorobenzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanesulfonamide | HCID 72879 | — |
| Reactant | Cyclopropanesulfonamide | HCID 15765418 | — |
| Reactant | 4-((2-Cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acid | HCID 86703655 | — |
| Reactant | 5-Cyclopropyl-4-((7,7-difluorobicyclo[4.1.0]heptan-1-yl)methoxy)-2-fluorobenzoic acid | HCID 86703676 | — |
| Product | 5-cyclopropyl-N-(cyclopropylsulfonyl)-4-(((1RS,6SR)-7,7-difluorobicyclo[4.1.0]heptan-1-yl)methoxy)-2-fluorobenzamide | HCID 86703736 | — |
Reaction Steps
Following the procedure as described in Example 332 Step 7 and making non-critical variations to replace 4-((2-cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acid with 5-cyclopropyl-4-(((1SR,6RS)-7,7-difluorobicyclo-[4.1.0]heptan-1-yl)methoxy)-2-fluorobenzoic acid and to replace methanesulfonamide with cyclopropanesulfonamide, the title compound was obtained as a white gum (0.053 g, 87%): 1H NMR (300 MHz, CDCl3) δ8.68 (d, J=14.5 Hz, 1H), 7.63 (d, J=9.1 Hz, 1H), 6.53 (d, J=14.1 Hz, 1H), 3.98 (s, 2H), 3.14-3.06 (m, 1H), 2.08-1.99 (m, 1H), 1.95-1.92 (m, 2H), 1.87-1.71 (m, 2H), 1.49-1.43 (m, 2H), 1.40-1.25 (m, 5H), 1.17-1.13 (m, 2H), 0.98-0.91 (m, 2H), 0.71-0.66 (m, 2H); MS (ES+) m/z 444.0 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08952169B2 |
| Source dataset | uspto-grants-2015_02 |
| ORD ID | ord-3288209b4dfd4f4182a8e8a99d36f6b3 |
| Source note | uspto-grants-2015_02 |