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 851949

Reaction equation

HRID 851949 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)i 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-c653123278c04365a7675c36d4d17247
Source dataset
uspto-grants-2007_08
Patent number
US07253169B2

Linked notes

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