HuagongsheHuagongshe Chemistry Print Report · For research reference only
Isopropylamine → 7-{[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl]-amino}-quinoline-8-carboxylic acid isopropylamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Isopropylamine | HCID 6363 | — |
| Reactant | Acetonitrile--water (1/1) | HCID 18373917 | — |
| Reactant | 2-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-3-oxa-1,5-diaza-phenanthren-4-one | HCID 57990152 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | 7-{[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl]-amino}-quinoline-8-carboxylic acid isopropylamide | HCID 57990128 | 71% |
Reaction Steps
To a suspension of 140 mg (0.28 mmol) of the above 2-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-3-oxa-1,5-diaza-phenanthren-4-one in 5.60 mL of a mixture acetonitrile: H2O 4:1 (v/v) is added 73 μL (0.85 mmol) of isopropylamine. The reaction mixture is stirred for 6 hours at ambient temperature. Brine is then added to the mixture and the product is extracted with ethyl acetate (3 times). The regrouped organic phases are dried on Na2SO4, filtrated and evaporated. The purification of the residue by flash chromatography (SiO2, heptane and ethyl acetate as eluants) affords 100 mg (70%) of a white solid; LC/MS: 503/505 (M+H)+, m.p.: 225-226° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08658801B2 |
| Source dataset | uspto-grants-2014_02 |
| ORD ID | ord-7f99ff1e1b9f41c1b25b8779833180f7 |
| Source note | uspto-grants-2014_02 |