Dimethylformamide → HCID 86644704, compound
Reaction equation
[Cl:1][C:2]1[C:10]([C:11]([C:14]#[N:15])([CH3:13])[CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].CN(C)C=O.C(Cl)(=O)C([Cl:24])=O>O1CCCC1>[Cl:1][C:2]1[C:10]([C:11]([C:14]#[N:15])([CH3:13])[CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([Cl:24])=[O:5]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2-chloro-3-(1-cyano-1-methylethyl)benzoic acid (157 mg, 0.705 mmol) produced in Example C61(v) in tetrahydrofuran (5 mL) were added N,N-dimethylformamide (20 μL) and oxalyl chloride (103 μL, 1.17 mmol), and the mixture was stirred at room temperature for 1.5 hr. The solvent was concentrated under reduced pressure to give 2-chloro-3-(1-cyano-1-methylethyl)benzoyl chloride. The present compound was dissolved in dimethylacetamide (5 mL), N-[5-(5-amino-2-methylphenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]cyclopropanecarboxamide (200 mg, 0.587 mmol) produced in Example C47(i) was added, and the mixture was stirred at room temperature for 20 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and filtered through a pad filled with silica gel. The solvent was concentrated under reduced pressure, and the obtained the residue was purified by silica gel column chromatography (ethyl acetate/hexane=0/100→70/30), and recrystallized from ethyl acetate and tetrahydrofuran to give the title compound (204 mg, 64%) as white crystals.
Workup
- concentrationThe solvent was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-9dfd087df0a44189a4aaa84a9feeca17
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08344135B2
Reaction notes
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