HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → HCID 178513703, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 2,6-Difluoro-3-nitrobenzoic acid | HCID 302629 | — |
| Reactant | 1H-pyrrolo(2,3-b)pyridin-5-amine | HCID 11715187 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | HCID 178513703 | HCID 178513703 | 88% |
Reaction Steps
5-Amino-7-azaindole (820 mg, 6.2 mmol), 2,6-difluoro-3-nitrobenzoic acid (1200 mg, 6.2 mmol), EDCI (1200 mg, 6.2 mmol), and HOBt.H2O (930 mg, 6.2 mmol) were combined in dry DMF (20 mL) and stirred at room temperature for 16 hours. The reaction mixture was then diluted with brine, extracted with EtOAc (2×), extracts washed with water (1×), dried over sodium sulfate and concentrated under reduced pressure. The resulting crude product was purified via silica gel chromatography using an ISCO system (5% MeOH/DCM) to provide 2,6-difluoro-5-nitro-(3H-imidazo[4,5-b]pyridin-6-yl)benzamide (1.76 g, 88%). m/z (LC-MS) M+1=319.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08338452B2 |
| Source dataset | uspto-grants-2012_12 |
| ORD ID | ord-a8ea201955984a27b0045bba99264836 |
| Source note | uspto-grants-2012_12 |