HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 1,2,3,4-Tetrahydro-1,8-naphthyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1,8-Naphthyridine | HCID 136069 | — |
| Reactant | Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate | HCID 151348 | — |
| Reactant | 1,2,3,4-Tetrahydro-1,8-naphthyridine | HCID 13047367 | — |
| Reactant | 5-Chloro-3-(4-chloro-3-trifluoromethyl benzenesulfonylamino)-pyridine-2-carboxylic acid | HCID 57942077 | — |
| Product | 1,2,3,4-Tetrahydro-1,8-naphthyridine | HCID 13047367 | — |
| Product | 4-chloro-N-[5-chloro-2-(3,4-dihydro-2H-[1,8]naphthyridine-1-carbonyl)-pyridin-3-yl]-3-trifluoromethyl-benzenesulfonamide | HCID 57942323 | — |
Reaction Steps
5-Chloro-3-(4-chloro-3-(trifluoromethyl)phenylsulfonamido)picolinic acid (208 mg, 0.50 mmol), 1,2,3,4-tetrahydro-[1,8]naphthyridine [(135 mg, 1.0 mmol) 1,2,3,4-tetrahydro-[1,8]naphthyridine was prepared freshly from 1,8-napthyridine via hydrogenation over Pt2O], BOP (486 mg, 1.1 mmol), DIEA (185 mg, 1.4 mmol) were reacted according to the procedure D to provide the title compound. HPLC purification (20→90% gradient of MeCN-water) provided 4-chloro-N[5-chloro-2-(3,4-dihydro-2H-[1,8]naphthyridine-1-carbonyl)-pyridin-3-yl]-3-trifluoromethyl-benzenesulfonamide: MS m/z: 531.0 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07622583B2 |
| Source dataset | uspto-grants-2009_11 |
| ORD ID | ord-de245f0304de47a18c8b6b06e14d6db9 |
| Source note | uspto-grants-2009_11 |