HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → N-(3-(3-(4-methoxyphenyl)-1-(6-(methylamino)pyrimidin-4-yl)-1H-indol-6-yl)phenyl)-3-morpholino-5-(trifluoromethyl)benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| 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 | 6-(6-(3-aminophenyl)-3-(4-methoxyphenyl)-1H-indol-1-yl)-N-methylpyrimidin-4-amine | HCID 50992002 | — |
| Reactant | 3-Morpholino-5-(trifluoromethyl)benzoate | HCID 86651380 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | N-(3-(3-(4-methoxyphenyl)-1-(6-(methylamino)pyrimidin-4-yl)-1H-indol-6-yl)phenyl)-3-morpholino-5-(trifluoromethyl)benzamide | HCID 50992088 | — |
Reaction Steps
HATU (100 mg, 0.260 mmol) was added to a mixture solution of 3-morpholino-5-(trifluoromethyl)benzoate (54 mg, 0.195 mmol), 6-(6-(3-aminophenyl)-3-(4-methoxyphenyl)-1H-indol-1-yl)-N-methylpyrimidin-4-amine (55 mg, 0.130 mmol) and DIPEA (45 μL, 0.26 mmol) in THF (2 mL) at room temperature. 12 hours later, the mixture was added to saturated sodium bicarbonate aqueous solution and then extracted with methylene chloride. The collected organic layer was washed with brine and then concentrated under reduced pressure by drying with anhydrous magnesium sulfate. The residue was purified by chromatography (preparative HPLC). The target compound was obtained as yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08329708B2 |
| Source dataset | uspto-grants-2012_12 |
| ORD ID | ord-54cb49254a1c4ccab06db7da91fc5c19 |
| Source note | uspto-grants-2012_12 |