HuagongsheHuagongshe Chemistry Print Report · For research reference only
(Pyrimidin-5-yl)boronic acid → (R)-N-(3-Fluoro-4-(trifluoromethoxy)phenyl)-6-(3-hydroxypyrrolidin-1-yl)-5-(pyrimidin-5-yl)nicotinamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (Pyrimidin-5-yl)boronic acid | HCID 2795193 | — |
| Reactant | (R)-5-bromo-N-(3-fluoro-4-(trifluoromethoxy)phenyl)-6-(3-hydroxypyrrolidin-1-yl)nicotinamide | HCID 86702607 | — |
| Product | (R)-N-(3-Fluoro-4-(trifluoromethoxy)phenyl)-6-(3-hydroxypyrrolidin-1-yl)-5-(pyrimidin-5-yl)nicotinamide | HCID 118195362 | — |
Reaction Steps
The title compound was prepared in an analogous fashion to that described in Example 185 using (R)-5-bromo-N-(3-fluoro-4-(trifluoromethoxy)phenyl)-6-(3-hydroxypyrrolidin-1-yl)nicotinamide (Stage 198.1) and pyrimidin-5-ylboronic acid to afford a white powder. HPLC (Condition 4) tR=4.88 min, UPLC-MS (Condition 3) tR=0.96 min, m/z=464.2 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.65-1.77 (m, 1H) 1.79-1.92 (m, 1H) 2.78-2.94 (m, 1H) 3.15-3.25 (m, 2H) 3.32-3.48 (m, 1H) 4.13-4.26 (m, 1H) 4.87 (d, J=3.52 Hz, 1H) 7.46-7.65 (m, 2H) 7.91-8.00 (m, 1H) 8.07 (d, J=2.35 Hz, 1H) 8.78 (d, J=2.35 Hz, 1H) 8.87 (s, 2H) 9.18 (s, 1H) 10.30 (s, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09278981B2 |
| Source dataset | uspto-grants-2016_03 |
| ORD ID | ord-240c0b7b1fd34879ad619d48249bdfd6 |
| Source note | uspto-grants-2016_03 |