HuagongsheHuagongshe Chemistry Print Report · For research reference only
Riluzole → 6-Fluoro-1-methyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carboxylic acid (2-methoxy-ethyl)-amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Riluzole | HCID 5070 | — |
| Reactant | 1,1'-Thiocarbonyldiimidazole | HCID 80264 | — |
| Reactant | 5-Amino-2-fluoro-N-(2-methoxy-ethyl)-4-methylamino-benzamide | HCID 67333319 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Product | 6-Fluoro-1-methyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carboxylic acid (2-methoxy-ethyl)-amide | HCID 86656773 | 33.7% |
Reaction Steps
6-Fluoro-1-methyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carboxylic acid (2-methoxy-ethyl)-amide (41 mg) was prepared by following General Procedure D starting from 5-amino-2-fluoro-N-(2-methoxy-ethyl)-4-methylamino-benzamide (72 mg), 2-amino-6-(trifluoromethoxy)-benzothiazole (59 mg), 1,1′-thiocarbonyldiimidazole (64 mg), and EDC (77 mg). LC/MS: m/z 484.8. 1H NMR (DMSO-d6, 400 MHz): δ 12.35 (bs, 1H), 8.16 (s, 1H), 7.91 (d, 1H), 7.88 (s, 1H), 7.73 (d, 1H), 7.50 (d, 1H), 7.36 (d, 1H), 3.61 (bs, 3H), 3.51-3.40 (m, 4H), 3.30 (s, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08759535B2 |
| Source dataset | uspto-grants-2014_06 |
| ORD ID | ord-2b7c7b118b7b47f591f0450cab1e5f80 |
| Source note | uspto-grants-2014_06 |