HuagongsheHuagongshe Chemistry Print Report · For research reference only
Riluzole → 3-Methyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-3H-imidazo[4,5-b]pyridine-6-carboxylic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Riluzole | HCID 5070 | — |
| Reactant | 1,1'-Thiocarbonyldiimidazole | HCID 80264 | — |
| Reactant | 5-Amino-6-methylamino-nicotinic acid ethyl ester | HCID 67334125 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Product | 3-Methyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-3H-imidazo[4,5-b]pyridine-6-carboxylic acid ethyl ester | HCID 58397766 | 40.8% |
Reaction Steps
3-Methyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-3H-imidazo[4,5-b]pyridine-6-carboxylic acid ethyl ester (560 mg) was prepared by following General Procedure D starting from 5-amino-6-methylamino-nicotinic acid ethyl ester (723 mg), 2-amino-6-(trifluoromethoxy)benzothiazole (735 mg), 1,1′-thiocarbonyldiimidazole (802 mg), and EDC (969 mg). LC/MS: m/z 437.8. 1H NMR (DMSO-d6, 400 MHz): δ 12.44 (s, 1H), 7.94 (s, 1H), 7.89 (s, 1H), 7.74 (s, 1H), 7.52 (d, 1H), 7.37 (d, 1H), 4.33 (q, 2H), 3.65 (s, 3H), 1.36 (t, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08759535B2 |
| Source dataset | uspto-grants-2014_06 |
| ORD ID | ord-8ab5e7ed019d4ef685b219e0480595c2 |
| Source note | uspto-grants-2014_06 |