Acetic Acid → 1-(4-butylphenyl)-3-cyclopropyl-5-hydroxypyridin-4(1H)-one

HRID 571049Notes

Reaction equation

HRID 571049 reaction equation
C([O:8][C:9]1[C:14](=[O:15])[C:13]([CH:16]2[CH2:18][CH2:17]2)=[CH:12][N:11]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH2:27][CH3:28])=[CH:21][CH:20]=2)[CH:10]=1)C1C=CC=CC=1.CC(O)=O>[Pd].CO>[CH2:25]([C:22]1[CH:21]=[CH:20][C:19]([N:11]2[CH:10]=[C:9]([OH:8])[C:14](=[O:15])[C:13]([CH:16]3[CH2:18][CH2:17]3)=[CH:12]2)=[CH:24][CH:23]=1)[CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 674199513-(benzyloxy)-1-(4-butylphenyl)-5-cyclopropylpyridin-4(1H)-one

Product 1

HCID 674185381-(4-butylphenyl)-3-cyclopropyl-5-hydroxypyridin-4(1H)-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 3-(benzyloxy)-1-(4-butylphenyl)-5-cyclopropylpyridin-4(1H)-one (27 mg, 0.07 mmol) and 10% Pd/C (1 mg, 0.001 mmol) in a 1:50 mixture of AcOH:MeOH was stirred under H2 (1 atm) for 18 h. The reaction mixture was filtered (0.5μ), concentrated under reduced pressure and purified by reversed phase HPLC (2 cm×5 cm C18, acetonitrile-water gradient, 0.05% TFA added) to provide 1-(4-butylphenyl)-3-cyclopropyl-5-hydroxypyridin-4(1H)-one. 1H NMR (499 MHz, DMSO): δ 7.73 (s, 1 H); 7.55 (d, J=2.7 Hz, 1 H); 7.48 (d, J=8.1 Hz, 2 H); 7.35 (d, J=8.1 Hz, 2 H); 2.64 (t, J=7.7 Hz, 2 H); 2.04-1.95 (m, 1 H); 1.61-1.52 (m, 2 H); 1.37-1.27 (m, 2 H); 0.94-0.87 (m, 3 H); 0.84-0.75 (m, 4 H). HRMS (ES) Calc (M+H)+=284.1645. Found 284.1643.

Workup

  1. filtrationThe reaction mixture was filtered (0.5μ)
  2. concentrationconcentrated under reduced pressure
  3. custompurified by reversed phase HPLC (2 cm×5 cm C18, acetonitrile-water gradient, 0.05% TFA added)

Sources & evidence

ORD record
ord-b2966d5b71de45428498eb2aeaaa01f0
Source dataset
uspto-grants-2015_05
Patent number
US09024032B2

Reaction notes

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