HuagongsheHuagongshe Chemistry Print Report · For research reference only
5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile → 5'-Cyano-2-(ethyl(2-hydroxyethyl)amino)-N-(4-((trifluoromethyl)thio)phenyl)-[3,3'-bipyridine]-5-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile | HCID 16414216 | — |
| Reactant | 5-bromo-6-(ethyl(2-hydroxyethyl)amino)-N-(4-((trifluoromethyl)thio)phenyl)nicotinamide | HCID 89906420 | — |
| Product | 5'-Cyano-2-(ethyl(2-hydroxyethyl)amino)-N-(4-((trifluoromethyl)thio)phenyl)-[3,3'-bipyridine]-5-carboxamide | HCID 118195302 | — |
Reaction Steps
The title compound was prepared in an analogous fashion to that described in Example 151 using 5-bromo-6-(ethyl(2-hydroxyethyl)amino)-N-(4-((trifluoromethyl)thio)phenyl)nicotinamide (Stage 195.1) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile to afford a yellow resin. UPLC-MS (Condition 3) tR=1.13 min, m/z=488.3 [M+H]+, m/z=486.3 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 0.90 (t, J=6.97 Hz, 3H) 3.15 (q, J=6.93 Hz, 2H) 3.36-3.40 (m, 2H) 3.44-3.56 (m, 2H) 4.55 (br. s, 1H) 7.70 (d, J=8.56 Hz, 2H) 7.85-7.99 (m, 2H) 8.10 (d, J=2.45 Hz, 1H) 8.53 (t, J=2.08 Hz, 1H) 8.79 (d, J=2.20 Hz, 1H) 9.04 (dd, J=4.03, 2.08 Hz, 2H) 10.36 (s, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09278981B2 |
| Source dataset | uspto-grants-2016_03 |
| ORD ID | ord-6598587370f34adfa2c7df2c777aec9d |
| Source note | uspto-grants-2016_03 |