Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1-Fluoro-4-(methylsulphonyl)benzene | HCID 67994 | — |
| Reactant | 1-Methyl-3-aminopyrazole | HCID 137254 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | ethyl 4-hydroxy-1-benzothiophene-6-carboxylate | HCID 11379055 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 66755939 | HCID 66755939 | — |
Reaction Steps
Cs2CO3 (0.806 g, 2.47 mmol) was added to a solution of ethyl 4-hydroxybenzo[b]thiophene-6-carboxylate (0.293 g, 1.24 mmol) and 1-fluoro-4-(methylsulfonyl)benzene (0.22 g, 1.26 mmol) in DMF (5 mL). The mixture was stirred at 120° C. for 8 hours and then cooled to room temperature. 1-Methyl-1H-pyrazol-3-amine (0.18 g, 1.85 mmol) and HATU (0.7 g, 1.85 mmol) were added. The reaction mixture was stirred at 50° C. for one hour and then filtered. Purification by HPLC gave a solid (107 mg, 20% yield) as expected product. 1 H NMR (400 MHz, DMSO-d6) δ 10.91 (s, 1 H) 8.51 (s, 1 H) 7.92-7.94 (m, 2 H) 7.71 (m, 1 H) 7.60-7.61 (m, 1 H) 7.20-7.23 (m, 2 H) 7.08-7.10 (m, 1 H) 6.58-6.59 (m, 1 H) 3.78 (s, 3 H), 3.21 (s, 3H), 2.58 (m, 3 H). LCMS for C21H19N3O4S2 m/z 442.10 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07842713B2 |
|---|
| Source dataset | uspto-grants-2010_11 |
|---|
| ORD ID | ord-3e1f3a5ff3484a389862dcf60b532881 |
|---|
| Source note | uspto-grants-2010_11 |
|---|
