Triethylamine → HCID 178472473, compound

HRID 1516152Notes

Reaction equation

HRID 1516152 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([O:12][C:13]2[N:14]=[N:15][C:16](Cl)=[CH:17][CH:18]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].C(N(CC)CC)C>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([O:12][C:13]2[N:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 178472462HCID 178472462, compound

Product 1

HCID 178472473HCID 178472473, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To an argon purged solution of cis/trans-4-(6-chloro-pyridazin-3-yloxy)-cyclohexanecarboxylic acid ethyl ester (1:1) (1.30 g, 4.57 mmol) and triethylamine (0.64 ml, 4.57 mmol) in ethyl acetate (46 ml) was added palladium on charcoal 10% (0.097 g). The reaction mixture was purged with hydrogen gas and stirred under an atmosphere of hydrogen gas for 4 h at room temperature. The catalyst and the ammonium salts were removed by filtration over Decalite. The filtrate was concentrated in vacuo to give the title compound (1.09 g, 95%) as light yellow oil.

Workup

  1. customThe reaction mixture was purged with hydrogen gas
  2. customThe catalyst and the ammonium salts were removed by filtration over Decalite
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-aa92cf19cfcb400c818084763a8d5c02
Source dataset
uspto-grants-2012_07
Patent number
US08227458B2

Reaction notes

Loading…