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2,2-Dimethyl-1,3-dioxane-4,6-dione → 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-(pyridin-3-yl)-5-(thiophen-3-yl)-3,4-dihydropyridin-2(1H)-one

HRID 924643
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HRID 924643 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7](=O)[CH2:8][C:9]2[CH:13]=[CH:12][S:11][CH:10]=2)[CH:2]=1.[CH2:15]([O:17][C:18]1[CH:19]=[C:20]([CH:23]=[C:24]([N+:27]([O-:29])=[O:28])[C:25]=1[OH:26])[CH:21]=O)[CH3:16].[CH3:30][C:31]1(C)[O:38]C(=O)CC(=O)O1.C([O-])(C)=O.[NH4+:44]>CC(O)=O>[CH2:15]([O:17][C:18]1[CH:19]=[C:20]([CH:21]2[C:8]([C:9]3[CH:13]=[CH:12][S:11][CH:10]=3)=[C:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[NH:44][C:31](=[O:38])[CH2:30]2)[CH:23]=[C:24]([N+:27]([O-:29])=[O:28])[C:25]=1[OH:26])[CH3:16]
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참가 물질

6

반응물 4

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 517165Ammonium AcetateHCID 5848783-Ethoxy-4-hydroxy-5-nitrobenzaldehydeHCID 610560411-(Pyridin-3-yl)-2-(thiophen-3-yl)ethanone

생성물 1

HCID 566442854-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-(pyridin-3-yl)-5-(thiophen-3-yl)-3,4-dihydropyridin-2(1H)-one수율 12%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A mixture of 1-(pyridin-3-yl)-2-(thiophen-3-yl)ethanone (Intermediate 1, see Example 18 for synthesic description of all intermediates) (230 mg, 1.1 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (296 mg, 1.4 mmol), meldrum's acid (202 mg, 1.4 mmol) and AcONH4 (108 mg, 1.4 mmol) in AcOH (3 mL) was refluxed under N2 overnight. The mixture was concentrated under reduced pressure and the residue was purified by prep-HPLC (0.1% TFA as additive) to give Compound 2 (60 mg, 12%). 1H NMR (MeOD 400 MHz): δ 8.70 (d, J=5.2 Hz, 1H), 8.67 (s, 1H), 8.30 (d, J=8.0 Hz, 1H), 7.90-7.62 (m, 1H), 7.72-7.60 (m, 1H), 7.27-7.24 (m, 2H), 6.94-6.92 (m, 1H), 6.58 (d, J=4.8 Hz, 1H), 4.20-4.11 (m, 3H), 3.30-3.25 (m, 1H), 2.79-2.74 (dd, J=16.2, 3.2 Hz, 1H), 1.45 (t, J=6.8 Hz, 3H). MS (ESI): m/z 438.3 [M+1]+.

후처리

  1. temperaturewas refluxed under N2 overnight
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customthe residue was purified by prep-HPLC (0.1% TFA as additive)

출처 및 근거

ORD 기록
ord-76daefcc4a0341bc8cd4ebfac59cbaa1
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09283213B2

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