Acetic Acid → 4-(2,2-dimethyl-3-tetrahydro-2H-pyrane-2-yloxypropionyl)-3-hydroxy-5-(2-methoxy-3-pyridyl)-1-(4-thiophene-3-ylphenyl)-1,5-dihydropyrrole-2-one

HRID 2037185Notes

Reaction equation

HRID 2037185 reaction equation
[CH3:1][C:2]([CH3:20])([CH2:12][O:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][O:15]1)[C:3](=[O:11])[CH2:4][C:5](=[O:10])[C:6]([O:8]C)=O.[S:21]1[CH:25]=[CH:24][C:23]([C:26]2[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=2)=[CH:22]1.[CH3:33][O:34][C:35]1[N:42]=[CH:41][CH:40]=[CH:39][C:36]=1[CH:37]=O.C(O)(=O)C>O1CCOCC1>[CH3:20][C:2]([CH3:1])([CH2:12][O:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][O:15]1)[C:3]([C:4]1[CH:37]([C:36]2[C:35]([O:34][CH3:33])=[N:42][CH:41]=[CH:40][CH:39]=2)[N:30]([C:29]2[CH:31]=[CH:32][C:26]([C:23]3[CH:24]=[CH:25][S:21][CH:22]=3)=[CH:27][CH:28]=2)[C:6](=[O:8])[C:5]=1[OH:10])=[O:11]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 41303364-(Thiophen-3-yl)anilineHCID 125333912-Methoxypyridine-3-carbaldehydeHCID 58365520methyl 5,5-dimethyl-2,4-dioxo-6-(tetrahydro-2H-pyrane-2-yloxy)hexanoate

Product 1

HCID 583653554-(2,2-dimethyl-3-tetrahydro-2H-pyrane-2-yloxypropionyl)-3-hydroxy-5-(2-methoxy-3-pyridyl)-1-(4-thiophene-3-ylphenyl)-1,5-dihydropyrrole-2-oneYield 55%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of methyl 5,5-dimethyl-2,4-dioxo-6-(tetrahydro-2H-pyrane-2-yloxy)hexanoate (0.29 mg, 1.0 mmol), 4-(3-thienyl)aniline (0.18 g, 1.0 mmol), 2-methoxynicotinaldehyde (0.14 g, 1.0 mmol), acetic acid (0.043 mL, 0.75 mmol) and dioxane (2 ml) was heated at reflux overnight. After the reaction was completed, the reaction mixture was concentrated in vacuo. The resulting residue was purified on a silica gel column chromatography (methanol/chloroform) to give 4-(2,2-dimethyl-3-tetrahydro-2H-pyrane-2-yloxypropionyl)-3-hydroxy-5-(2-methoxy-3-pyridyl)-1-(4-thiophene-3-ylphenyl)-1,5-dihydropyrrole-2-one (0.30 g, yield: 55%) as pale yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. customThe resulting residue was purified on a silica gel column chromatography (methanol/chloroform)

Sources & evidence

ORD record
ord-1a41777bb09849a2af1fe88869c6a524
Source dataset
uspto-grants-2013_11
Patent number
US08575197B2

Reaction notes

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