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 7-hydroxybenzo[b]thiophene-5-carboxylate | HCID 11310602 | — |
| Reactant | 2,4-difluoro-N,N-dimethylbenzamide | HCID 60637230 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 59560438 | HCID 59560438 | — |
Reaction Steps
Cs2CO3 (0.806 g, 2.47 mmol) was added to a solution of ethyl 7-hydroxybenzo[b]thiophene-5-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 (56 mg, 10% yield) as expected product. 1H NMR (400 MHz, DMSO-d6) δ 10.90 (s, 1 H) 8.51 (m, 1 H) 8.23 (s, 1 H) 8.07-8.09 (d, 1 H)) 7.93-7.94 (m, 1 H) 7.67-7.70 (m, 3 H) 7.41-7.46 (t, 1 H) 7.15-7.17 (m, 1 H) 7.00-7.03 (m, 1H) 3.00 (s, 3 H) 2.88 (m, 3 H) 2.29 (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-f4ccbd0f89184877ba2b8a9a61e5702b |
|---|
| Source note | uspto-grants-2010_11 |
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