(E)-tert-butyl 3-(6,6-dimethyl-7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylate → (E)-3-(6,6-dimethyl-7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic acid

HRID 2175750Notes

Reaction equation

[CH3:1][C:2]1([CH3:22])[C:11](=[O:12])[NH:10][C:9]2[N:8]=[CH:7][C:6](/[CH:13]=[CH:14]/[C:15]([O:17]C(C)(C)C)=[O:16])=[CH:5][C:4]=2[CH2:3]1>C(Cl)Cl>[CH3:1][C:2]1([CH3:22])[C:11](=[O:12])[NH:10][C:9]2[N:8]=[CH:7][C:6](/[CH:13]=[CH:14]/[C:15]([OH:17])=[O:16])=[CH:5][C:4]=2[CH2:3]1

Participants

Conditions

Temperature: 27.5 °C

Procedure

To a stirred solution of (E)-tert-butyl 3-(6,6-dimethyl-7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylate (W) (1.2 g, 3.97 mmol) in CH2Cl2 (10 mL) was added trifluoro acetic aid (5 mL) at 20-35° C. and the reaction mixture was allowed to stir at 20-35° C. for 3 h. Then the reaction mixture was rotary evaporated under vacuum to get residue which was triturated with diethyl ether to get the desired compound as an off-white solid (700 mg, 77%); 1H NMR (400 MHz, DMSO-d6) δ 10.66 (s, 1H), 8.37 (d, J=2.0 Hz, 1H), 8.01 (s, 1H), 7.55 (d, J=16.1 Hz, 1H), 6.51 (d, J=15.6 Hz, 1H), 2.80 (s, 2H), 1.08 (s, 6H).

Workup

customThen the reaction mixture was rotary evaporated under vacuum
customto get residue which
customwas triturated with diethyl ether

Sources & evidence

ORD record: ord-5474e86dd2b643dea652b4dce4b196cd
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09062075B2

Reaction notes

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