2-Ethylpropanedioyl dichloride → Ethyl 4-hydroxy-1-methyl-2-oxo-7-(trifluoromethyl)-1,2-dihydro-1,8-naphthyridine-3-carboxylate

HRID 1801986Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C:6]([N:8]([C:10]1[N:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:11]=1[C:12]([O:14]C)=O)[CH3:9])=[O:7])[CH3:2].CNC1N=C(C(F)(F)F)C=CC=1C(OC)=O.C(C(C(Cl)=O)C(Cl)=O)C>ClCCCl>[OH:14][C:12]1[C:11]2[C:10](=[N:19][C:18]([C:20]([F:23])([F:22])[F:21])=[CH:17][CH:16]=2)[N:8]([CH3:9])[C:6](=[O:7])[C:5]=1[C:4]([O:3][CH2:1][CH3:2])=[O:24]

Participants

Conditions

Temperature: 80 °C

Procedure

Methyl 2-(3-ethoxy-N-methyl-3-oxopropanamido)-6-(trifluoromethyl)nicotinate. A mixture of methyl 2-(methylamino)-6-(trifluoromethyl)nicotinate (0.300 g) and ethyl malonoyl chloride (0.19 mL, 1.6 mmol) in 1,2-dichloroethane (50 mL) was heated to 80° C. for 63 hours. The reaction mixture was allowed to reach room temperature and was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (gradient: 0-30% EtOAc/hexanes) to give the title compound. MS (ESI, pos. ion) m/z: 349 (M+1).

Workup

customto reach room temperature
customwas then evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (gradient: 0-30% EtOAc/hexanes)

Sources & evidence

ORD record: ord-6d147c0ed63041f3bbd432cdfb0da141
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349868B2

Reaction notes

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