Potassium Phosphate, Tribasic → 1-Biphenyl-2-ylmethyl-4-oxo-1,4-dihydro-[1,5]naphthyridine-3-carboxylic acid ethyl ester

HRID 1497670

Reaction equation

[CH2:1]([O:3][C:4](=[O:19])[C:5]([C:10]([C:12]1[C:17](F)=[CH:16][CH:15]=[CH:14][N:13]=1)=[O:11])=[CH:6][N:7]([CH3:9])C)[CH3:2].[O-]P([O-])([O-])=O.[K+].[K+].[K+].[C:28]1([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1CN>CC(N(C)C)=O>[CH2:1]([O:3][C:4]([C:5]1[C:10](=[O:11])[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][N:13]=2)[N:7]([CH2:9][C:41]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:6]=1)=[O:19])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred solution of 3-dimethylamino-2-(3-fluoro-pyridine-2-carbonyl)acrylic acid ethyl ester (4) (18 mg, 0.067 mmol) in dimethylacetamide (2 mL) was added K3PO4 (28 mg, 0.14 mmol) followed by C-biphenyl-2-yl-methylamine (5) (11 mg, 0.06 mmol) at room temperature. The mixture was stirred at 70° C. for 14 h. After completion of the reaction, the reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and concentrated. The residue was purified using normal silica gel column chromatography (3% methanol:dichloromethane) to get 1-biphenyl-2-ylmethyl-4-oxo-1,4-dihydro-[1,5]naphthyridine-3-carboxylic acid ethyl ester (6) (9 mg, 35%) as a sticky solid.

Workup

customAfter completion of the reaction
extractionextracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated
customThe residue was purified

Sources & evidence

ORD record: ord-6406fe521e4d4ccfb033b50462a02d1c
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199987B2

Linked notes

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