Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Thionyl Chloride | HCID 24386 | — |
| Reactant | 2-Methyl-1,3-thiazole-4-carboxylic acid | HCID 284728 | — |
| Reactant | 4-Aminopyridazine | HCID 298492 | — |
| Catalyst | Dimethylformamide | HCID 6228 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 50902981 | HCID 50902981 | — |
Reaction Steps
250 mg (1.8 mmol) of 2-Methyl-thiazole-4-carboxylic acid were suspended in 20 mL of toluene and two drops of dimethylformamide were added to the mixture. 0.16 mL of thionylchloride (2.2 mmol) were added at room temperature and the reaction mixture was stirred at 65° C. for two hours. After removal of the solvent, toluene was added and the evaporation was repeated. The obtained residue was then dissolved in 10 mL of dichloromethane and the solution was added dropwise to a solution containing 166 mg pyridazin-4-yl-amine (1.8 mmol) and 0.27 ml triethyl amine (1.9 mmol) in 40 ml dichloromethane. The mixture was stirred at room temperature for 16 h and the solvent was removed under vacuum. The obtained residue was purified by flash column chromatography (silica, gradient elution cyclohexane, ethyl acetate, methanol) to give 50 mg (13%, 99% purity) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09029639B2 |
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| Source dataset | uspto-grants-2015_05 |
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| ORD ID | ord-e74c1e3497094ae2adcec28d951054bc |
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| Source note | uspto-grants-2015_05 |
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