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

HRID 924644
Notes
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Reaction equation

HRID 924644 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7](=O)[CH2:8][C:9]2[CH:13]=[CH:12][S:11][CH:10]=2)[CH:4]=[N:3]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:5]3[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 517165Ammonium AcetateHCID 5848783-Ethoxy-4-hydroxy-5-nitrobenzaldehydeHCID 651957941-(1-methyl-1H-pyrazol-4-yl)-2-(thiophen-3-yl)ethanone2×

Product 1

HCID 566442874-(3-ethoxy-4-hydroxy-5-nitrophenyl)-6-(1-methyl-1H-pyrazol-4-yl)-5-(thiophen-3-yl)-3,4-dihydropyridin-2(1H)-one
Yield 6.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1-(1-methyl-1H-pyrazol-4-yl)-2-(thiophen-3-yl)ethanone (Intermediate 3) (150 mg, 0.73 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (185 mg, 0.87 mmol), meldrum's acid (125 mg, 0.87 mmol) and AcONH4 (84 mg, 1.1 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 4 as yellow solid (20 mg, 6%). 1H NMR (DMSO-d6, 400 MHz): δ 10.20 (s, 1H), 9.43 (s, 1H), 7.62 (s, 1H), 7.42-7.36 (m, 2H), 7.19-7.11 (m, 1H), 7.06 (s, 2H), 6.70-6.68 (m, 1H), 4.11-4.03 (m, 2H), 3.95-3.92 (m, 1H), 3.77 (s, 3H), 3.08 (dd, J=16.4, 7.6 Hz, 1H), 2.60-2.52 (m, 1H), 1.34 (t, J=6.8 Hz, 3H). MS (ESI): m/z 440.9 [M+1]+.

Workup

  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)

Sources & evidence

ORD record
ord-8060c65a13d6473d8c96945e6b3bb47f
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09283213B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes