Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| 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 | — |
| Reactant | 2,4-difluoro-N,N-dimethylbenzamide | HCID 60637230 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 59560107 | HCID 59560107 | — |
Reaction Steps
Cs2CO3 (0.806 g, 2.47 mmol) was added to a solution of ethyl 4-hydroxybenzo[b]thiophene-6-carboxylate (0.275 g, 1.24 mmol) and 2,4-difluoro-N,N-dimethylbenzamide (0.234 g, 1.26 mmol) in DMF (5 ML). The mixture was stirred at 150° C. for 10 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 (200 mg, 38% yield) as expected product. 1H NMR (400 MHz, DMSO-d6) δ 10.96 (s, 1 H) 8.59 (m, 1 H) 8.00 (m, 1 H)) 7.61-7.68 (m, 2 H) 7.39-7.43 (m, 2 H) 7.08-7.11 (m, 1 H) 6.92-6.95 (m, 1 H) 6.60 (s, 1 H) 3.79 (s, 3 H) 3.00 (s, 3 H) 2.88 (m, 3 H). LCMS for C22H19FN4O3S m/z 439.10 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08119624B2 |
|---|
| Source dataset | uspto-grants-2012_02 |
|---|
| ORD ID | ord-c13b39db4f5347eea67aae9b80abbb9d |
|---|
| Source note | uspto-grants-2012_02 |
|---|
