Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-Amino-5-methylpyridine | HCID 15348 | — |
| 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 59559881 | HCID 59559881 | — |
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 (0.286 g, 1.55 mmol) in DMF (5 mL). The mixture was stirred at 150° C. for 8 hours and then cooled to room temperature. 2-Amino-5-methyl pyridine (0.228 g, 2.11 mmol) and then HATU (0.7 g, 1.85 mmol) were added. The reaction mixture was stirred at 75° C. for four hours and then filtered. Purification by HPLC gave a solid (57 mg, 10% yield) as expected product. 1H NMR (400 MHz, DMSO-d6) δ 10.84 (s, 1 H) 8.64 (s, 1 H) 8.22 (m, 1 H) 8.07-8.09 (d, 1 H)) 8.01-8.02 (d, 1 H) 7.69 (m, 1 H) 7.65-7.68 (m, 1 H) 7.39-7.43 (m, 2 H) 7.08-7.11 (m, 1 H) 6.93-6.95 (m, 1 H) 2.99 (s, 3 H) 2.87 (m, 3 H) 2.28 (s, 3 H). LCMS for C24H20FN3O3S m/z 450.10 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07842713B2 |
|---|
| Source dataset | uspto-grants-2010_11 |
|---|
| ORD ID | ord-98a76eb958214396b8aa6b82ff4bb1ab |
|---|
| Source note | uspto-grants-2010_11 |
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