HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → HCID 86711423, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | N-(Propan-2-yl)pyridine-2-carbohydrazonic acid | HCID 3041746 | — |
| 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 | HCID 11323657 | HCID 11323657 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86711423 | HCID 86711423 | — |
Reaction Steps
To solution containing (E)-3-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)acrylic acid (200 mg, 0.696 mmol), N′-isopropyl picolino hydrazide (187.14 mg, 1.04 mmol) and HATU (397.02 mg, 1.04 mmol) dissolved in DMF (7.0 ml), N,N-diisopropylethylamine (DIPEA)(0.1819 ml, 1.04 mmol) was slowly drop-wise added and stirred at room temperature for 12 hr. The reaction mixture was diluted with EtOAc, washed with water and brine, dried with anhydrous MgSO4 filtered, filtered, and concentrated under reduced pressure. The residue was separated through silica gel chromatography (n-hexane:EtOAc=3:1) dried so that the ivory (E)-tert-butyl 3-(3-(1-isopropyl-2-picolinoyl hydrazinyl)-3-oxoprop-1-enyl)-1H-indole-1-carboxylate was obtained (108.1 mg, 34.6%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08906952B2 |
| Source dataset | uspto-grants-2014_12 |
| ORD ID | ord-b4056cb176704a6cb38793326e15cb75 |
| Source note | uspto-grants-2014_12 |