Hydrochloric Acid → HCID 19354338, compound
Reaction equation
NC1C(C(=O)C)=CC=CN=1.C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C.C([O:31][C:32]1([CH3:46])[O:37][C:36]([C:38]([CH3:41])([CH3:40])[CH3:39])=[N:35][C:34]2[N:42]=[CH:43][CH:44]=[CH:45][C:33]1=2)(=O)C(C)(C)C.Cl>CN(C)C1C=CN=CC=1.O.C1(C)C=CC=CC=1>[C:32]([C:33]1[C:34]([NH:35][C:36](=[O:37])[C:38]([CH3:41])([CH3:40])[CH3:39])=[N:42][CH:43]=[CH:44][CH:45]=1)(=[O:31])[CH3:46]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 60 °C
Procedure
To a mixture of 1-(2-aminopyridin-3-yl)ethanone (272 mg, 2 mmol), 4-dimethylaminopyridine (24 mg, 0.2 mmol), triethylamine (0.64 mL, 4.6 mmol) and toluene (2 mL) was added pivaloyl chloride (0.52 mL, 4.2 mmol) dropwise at room temperature, which was stirred at room temperature for one hour and at 60° C. for five hours. After formation of 2-tert-butyl-4-methyl-4H-pyrido[2,3-d][1,3]oxazin-4-yl pivalate was confirmed, to the reaction mixture were added water (2 mL) and 5N hydrochloric acid (0.8 mL), which was stirred at room temperature for 30 minutes. After the reaction mixture was separated, to the aqueous layer was added 5N aqueous sodium hydroxide (1 mL) and extracted with toluene. The solvent was evaporated under a reduced pressure and the precipitated solid was filtered to obtain the title compound (415 mg).
Workup
- stirringwas stirred at room temperature for 30 minutes
- customAfter the reaction mixture was separated, to the aqueous layer
- additionwas added 5N aqueous sodium hydroxide (1 mL)
- extractionextracted with toluene
- customThe solvent was evaporated under a reduced pressure
- filtrationthe precipitated solid was filtered
Sources & evidence
- ORD record
- ord-2f8457a522674a70bf1c759e671e6b0f
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08513287B2
Reaction notes
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