Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dibutylamine | HCID 8148 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 6-Bromopyridine-2-carboxylic acid | HCID 593919 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86718950 | HCID 86718950 | 72% |
Reaction Steps
To a solution of 6-bromopicolinic acid (Aldrich, 404 mg, 2.00 mmol) in DMF (3.0 mL) were added dibutylamine (Aldrich, 258 mg, 2.00 mmol), HATU (760 mg, 2.00 mmol) and DIEA (1.1 mL, 6.00 mmol). The reaction mixture was stirred at room temperature for 3 h and then quenched by adding sat. aq. NH4Cl solution. The mixture was extracted with EtOAc (3×). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash column chromatography, gradient from 0 to 20% EtOAc/DCM to give a light brown oil (450 mg, 72%). 1H NMR (CDCl3) δ 7.67-7.57 (m, 2H), 7.51 (dd, J=7.5, 1.3 Hz, 1H), 3.53-3.42 (m, 2H), 3.36-3.27 (m, 2H), 1.72-1.56 (m, 4H), 1.46-1.33 (m, 2H), 1.27-1.15 (m, 2H), 0.97 (t, J=7.4 Hz, 3H), 0.85 (t, J=7.4 Hz, 3H); MS(ESI+) m/z 313.2 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09346795B2 |
|---|
| Source dataset | uspto-grants-2016_05 |
|---|
| ORD ID | ord-65cda412c3d440eeb1cb8b10a283f71d |
|---|
| Source note | uspto-grants-2016_05 |
|---|
