2-Pyridone → HCID 11781538, compound

HRID 1760183Notes

Reaction equation

HRID 1760183 reaction equation
N1C=CC=CC1=O.C/C=C/CCCCC1OC2N(CC/C/2=N/O)C(=O)C=1C.Cl.[CH3:29][Si:30]([CH3:45])([C:41]([CH3:44])([CH3:43])[CH3:42])[O:31][CH:32]([CH:36]([O:39][CH3:40])[O:37][CH3:38])[CH2:33][CH2:34][NH2:35].C[Si](C)(C(C)(C)C)OC(C(OC)OC)CC#N>C(O)C.O=[Pt]=O.C(Cl)(Cl)Cl>[CH3:45][Si:30]([CH3:29])([C:41]([CH3:43])([CH3:42])[CH3:44])[O:31][CH:32]([CH:36]([O:39][CH3:40])[O:37][CH3:38])[CH2:33][CH2:34][NH2:35]

Participants

8

Reactant 4

HCID 88712-Pyridone3×HCID 10869008HCID 10869008, compound2×HCID 86759587HCID 86759587, compoundHCID 100945420HCID 100945420, compound

Product 1

HCID 11781538HCID 11781538, compound

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalyst2×HCID 702EthanolSolvent3×HCID 6212ChloroformSolvent2×

Procedure

Pyridinone derivative (R) can be reduced to form pyridinone derivative (T) as shown in Reaction Scheme X. A similar result in Reaction Scheme X can be obtained for the corresponding derivative of pyridinone (E). wherein Z, R2, R3, and R4 are as defined in Reaction Scheme VI. The reduction of the nitrile substituted pyridinone derivative (R) is accomplished by combining PtO2 and the nitrile substituted pyridinone in dry ethanol and adding CHCl3. The combined reaction mixture is agitated under hydrogen pressure at room temperature for about 24 hours. The preparation of pyridinone derivative (T) is illustrated by a procedure described by Clive D. L. J., Hisaindee, S., J. Org. Chem. 2000, 65: 4923-4929 in their synthesis of racemic brevioxime and related model compounds, the entirety of which is hereby incorporated by reference. The authors describe the preparation of 3-[[Dimethyl(1,1-dimethylethyl)silyl]oxy]-4,4-dimethoxybutanamine Hydrochloride from 3-[[Dimethyl(1,1-dimethylethyl)silyl]oxy]-4,4-dimethoxybutanenitrile. A solution of 3-[[Dimethyl(1,1-dimethylethyl)silyl]oxy]-4,4-dimethoxybutanenitrile in dry ethanol was added to a suspension of Adam's catalyst in dry ethanol, followed by the addition of bench CHCl3. The mixture was shaken under hydrogen at room temperature for 24 hours. The catalyst was filtered off and the filtrate was evaporated. The residue was kept under oil pump vacuum for 24 hours to give 3-[[Dimethyl(1,1-dimethylethyl)silyl]oxy]-4,4-dimethoxybutanamine.

Workup

  1. customas shown in Reaction Scheme X
  2. customA similar result in Reaction Scheme X
  3. customas defined in Reaction Scheme VI
  4. customThe combined reaction mixture
  5. stirringThe mixture was shaken under hydrogen at room temperature for 24 hours
  6. filtrationThe catalyst was filtered off
  7. customthe filtrate was evaporated
  8. waitThe residue was kept under oil pump vacuum for 24 hours

Sources & evidence

ORD record
ord-d4da34f069e74922a540e379f3cdaed2
Source dataset
uspto-grants-2005_01
Patent number
US06841559B1

Reaction notes

Loading…