HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Thiazolamine, 4-(trifluoromethyl)- → 6-{(E)-2-[3-Difluoromethoxy-2-(2,2-dimethylpropoxy)phenyl]vinyl}-N-[4-(trifluoro-methyl)-1,3-thiazol-2-yl]imidazo[2,1-b][1,3]thiazole-5-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Thiazolamine, 4-(trifluoromethyl)- | HCID 1201417 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 6-{(E)-2-[3-(Difluoromethoxy)-2-(2,2-dimethylpropoxy)phenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxylic acid | HCID 68407345 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 6-{(E)-2-[3-Difluoromethoxy-2-(2,2-dimethylpropoxy)phenyl]vinyl}-N-[4-(trifluoro-methyl)-1,3-thiazol-2-yl]imidazo[2,1-b][1,3]thiazole-5-carboxamide | HCID 46833252 | — |
Reaction Steps
The title compound was prepared according to the general procedure (Method B) by coupling Intermediate 7A (270 mg, 0.639 mmol) with 4-(trifluoromethyl)-1,3-thiazol-2-amine (116 mg, 0.703 mmol) in the presence of EDCI hydrochloride (245 mg, 1.278 mmol) and DMAP (72 mg, 0.639 mmol) in a mixture of THF and DMF (1:1, 6 mL) to give 127 mg of the product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.02 (s, 9H), 3.56 (s, 2H), 7.17 (t, J=74.1 Hz, 1H), 7.20-7.31 (m, 2H), 7.42-7.45 (m, 1H), 7.52 (d, J=15.9 Hz, 1H), 7.67-7.69 (m, 1H), 7.81 (d, J=16.2 Hz, 1H), 8.06-8.10 (m, 2H), 13.01 (br s, 1H); APCI-MS (m/z) 573.26 (MH)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08318928B2 |
| Source dataset | uspto-grants-2012_11 |
| ORD ID | ord-85ed9f5653a24b5d95286b5d609dec7a |
| Source note | uspto-grants-2012_11 |