Triethylamine → HCID 50902981, compound
Reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([OH:9])=O)[N:6]=1.S(Cl)(Cl)=O.[N:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][N:15]=1.[CH2:21](N(CC)CC)C>C1(C)C=CC=CC=1.CN(C)C=O.ClCCl>[CH3:21][N:20]([C:17]1[CH:18]=[CH:19][N:14]=[N:15][CH:16]=1)[C:7]([C:5]1[N:6]=[C:2]([CH3:1])[S:3][CH:4]=1)=[O:9]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 65 °C
Procedure
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.
Workup
- customAfter removal of the solvent, toluene
- additionwas added
- customthe evaporation
- dissolutionThe obtained residue was then dissolved in 10 mL of dichloromethane
- additionthe solution was added dropwise to a solution
- stirringThe mixture was stirred at room temperature for 16 h
- customthe solvent was removed under vacuum
- customThe obtained residue was purified by flash column chromatography (silica, gradient elution cyclohexane, ethyl acetate, methanol)
Sources & evidence
- ORD record
- ord-e74c1e3497094ae2adcec28d951054bc
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09029639B2
Reaction notes
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