Triethylamine → HCID 131735948, compound
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]=[CH:9][C:10]([OH:12])=O)[CH:3]=1.Cl.[CH3:14][NH:15][O:16][CH3:17].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.C(N(CC)CC)C>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]=[CH:9][C:10]([N:15]([O:16][CH3:17])[CH3:14])=[O:12])[CH:3]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
3-(4-Bromo-pyridin-2-yl)-acrylic acid (6.3 g, 27.6 mmol) prepared in Step 1, N,O-dimethylhydroxylamine hydrochloride (3.0 g, 30.4 mmol), HOBT (7.5 g, 55.3 mmol), EDAC (10.6 g, 55.3 mmol) and triethylamine (11.5 mL, 82.9 mmol) were added to N,N-dimethylformamide (100.0 mL). The reaction mixture was stirred at room temperature for 18 hours, quenched with a saturated solution of ammonium chloride, and then extracted with ethyl acetate. The extract was washed with brine, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a yellow liquid residue. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=2/1) to give 2.4 g of the titled compound as a pale yellow solid.
Workup
- customquenched with a saturated solution of ammonium chloride
- extractionextracted with ethyl acetate
- washThe extract was washed with brine
- dry with materialdried on anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customto give a yellow liquid residue
- customThe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=2/1)
Sources & evidence
- ORD record
- ord-ea775fbcac1e46d885f08e91f3e706ec
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09376420B2
Reaction notes
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