Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 2-Bromopyridine | HCID 7973 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | (4-Methanesulfonyl-phenyl)-[5-nitro-6-(piperidin-4-yloxy)-pyrimidin-4-yl]-amine | HCID 11257886 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 11328888 | HCID 11328888 | — |
Reaction Steps
Compound A2 (0.13 mmol, 50 mg), and 2-bromo-pyridine (0.53 mmol, 53 μL) were dissolved in DMF (1 mL) and triethylamine (0.46 mmol, 63 μL). The reaction was heated in a microwave at 165° C. for 40 minutes. The mixture was quenched with water and extracted with ethyl acetate. Removal of organic solvent in vacuo and purification by prep-TLC provided Compound A9 as a yellow solid (12 mg, 20%). 1H NMR (400 MHz, CDCl3) δ (ppm): 10.10 (s, 1H), 8.35 (s, 1H), 8.13 (m, 1H), 7.89 (d, 2H), 7.81 (d, 2H), 7.42 (m, 1H), 6.64 (d, 1H), 6.55 (m, 1H), 5.58 (heptet, 1H), 3.78 (m, 2H), 3.60 (m, 2H), 3.00 (s, 3H), 2.02 (m, 2H), 1.91 (m, 2H). LCMS (ESI), m/z 471.4 (M+H+, 100%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08546429B2 |
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| Source dataset | uspto-grants-2013_10 |
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| ORD ID | ord-3de65073154e40f9af0d59fbcd3eea62 |
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| Source note | uspto-grants-2013_10 |
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