HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 8-[(2,6-Difluorobenzyl)oxy]-6-ethynyl-N-[(2R)-hydroxyhexan-2-yl]-2-methylimidazo[1,2-a]-pyridine-3-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | (R)-2-Aminohexan-1-ol | HCID 6994402 | — |
| 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 | 8-[(2,6-Difluorobenzyl)oxy]-6-ethynyl-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid | HCID 86718173 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 8-[(2,6-Difluorobenzyl)oxy]-6-ethynyl-N-[(2R)-hydroxyhexan-2-yl]-2-methylimidazo[1,2-a]-pyridine-3-carboxamide | HCID 86718224 | — |
Reaction Steps
Under argon, 50 mg (0.15 mmol) of 8-[(2,6-difluorobenzyl)oxy]-6-ethynyl-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid were dissolved in 0.5 ml of dry dimethylformamide, 20.54 mg (0.18 mmol, 1.2 equivalents) of (R)-(−)-2-aminohexanol, 72 μl of diisopropylethylamine (0.44 mmol, 3 equivalents) and 72 mg of HATU (0.19 mmol, 1.3 equivalents) were added and the mixture was stirred at room temperature overnight. A little water was then added, and the mixture was purified directly by preparative HPLC (Method 8). This gave 37.5 mg of the target compound (58% of theory).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08946215B2 |
| Source dataset | uspto-grants-2015_02 |
| ORD ID | ord-f6e3be61185a4272a44e1ae3a845c84e |
| Source note | uspto-grants-2015_02 |