(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 2175750노트

반응식

HRID 2175750 반응식
[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

참가 물질

3

반응물 1

HCID 59277606(E)-tert-butyl 3-(6,6-dimethyl-7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylate

생성물 1

HCID 59277535(E)-3-(6,6-dimethyl-7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic acid수율 77%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
27.5 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-5474e86dd2b643dea652b4dce4b196cd
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062075B2

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