3,3-Dimethyl-1-[2-(6-(3-pyridyl)hex-5 ynoyl)perhydropyridazinyl] pentane-1,2-dione → 3,3-Dimethyl-1-[2-(6-(3-pyridyl)-hexanoyl)perhydropyridazinyl] pentane-1,2-dione

HRID 2228460Notes

Reaction equation

HRID 2228460 reaction equation
[CH3:1][C:2]([CH3:28])([CH2:26][CH3:27])[C:3](=[O:25])[C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][NH:8][N:7]1[C:12](=[O:24])[CH2:13][CH2:14][CH2:15][C:16]#[C:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)=[O:5]>CO.O=[Pt]=O>[CH3:1][C:2]([CH3:28])([CH2:26][CH3:27])[C:3](=[O:25])[C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][NH:8][N:7]1[C:12](=[O:24])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)=[O:5]

Participants

4

Reactant 1

HCID 184700723,3-Dimethyl-1-[2-(6-(3-pyridyl)hex-5 ynoyl)perhydropyridazinyl] pentane-1,2-dione

Product 1

HCID 184700753,3-Dimethyl-1-[2-(6-(3-pyridyl)-hexanoyl)perhydropyridazinyl] pentane-1,2-dione

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

0.1 g PtO2 was added to a solution of 3,3-dimethyl-1-[2-(6-(3-pyridyl)hex-5 ynoyl)perhydropyridazinyl]pentane-1,2-dione (0.3 g, 0.8 mmol) in 20 ml dry MeOH. The mixture was under hydrogenation at room pressure (1 atm) overnight. The product was obtained as clear oil after filtering the catalyst, concentration and purifying on a silica gel (0.125 g, 41%). Rf=0.18 (EtOAc). 1H NMR (CDCl3, 400 MHz): δ 0.89 (t, 3H, J=7.4); 1.24 (s, 6H); 1.38 (m, 2H); 1.66 (m, 10H); 2.14 (m, 2H); 2.63 (m, 2H); 2.82 (m, 2H); 4.60 (m, 2H); 7.23 (m, 4H). Anal. Calcd. for C22H33N3O3: C, 68.19; H, 8.58; N, 10.84. Found: C, 68.40; H, 8.52; N, 10.62.

Workup

  1. customwas under hydrogenation at room pressure (1 atm) overnight
  2. customThe product was obtained as clear oil
  3. filtrationafter filtering
  4. concentrationthe catalyst, concentration
  5. custompurifying on a silica gel (0.125 g, 41%)

Sources & evidence

ORD record
ord-39bcde630f15426faf769ffb6287ad75
Source dataset
uspto-grants-2002_07
Patent number
US06417189B1

Reaction notes

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