Triethylamine → HCID 14013780, compound

HRID 1649659Notes

Reaction equation

HRID 1649659 reaction equation
Cl[C:2]([F:26])([F:25])[C:3]1[N:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:5]([O:18][CH2:19][CH3:20])[C:4]=1[C:21]([O:23][CH3:24])=[O:22].C(N(CC)CC)C>C(O)C.[Pd]>[F:26][CH:2]([F:25])[C:3]1[N:8]=[C:7]([C:9]([F:12])([F:10])[F:11])[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:5]([O:18][CH2:19][CH3:20])[C:4]=1[C:21]([O:23][CH3:24])=[O:22]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 14013778HCID 14013778, compound

Product 1

HCID 14013780HCID 14013780, compoundYield 47.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5.0 g (0.012 mol) of product of Example 19, 1.72 ml (0.012 mol) of triethylamine and 0.75 g of 10% Pd-C in 65 ml of ethanol was hydrogenated at 40° C. under 522 kPa of H2 pressure for 18 hours. The reaction mixture was filtered through celite and concentrated. The residue was taken up in ether, washed with 10% HCl (aq), dried (MgSO4) and concentrated in vacuo to 3.28 g of yellow solid, which was recrystallized in hot hexane to give 2.13 g (47.4%) of product as a light yellow solid, mp 59°-61° C.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationconcentrated
  3. washwashed with 10% HCl (aq)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo to 3.28 g of yellow solid, which
  6. customwas recrystallized in hot hexane

Sources & evidence

ORD record
ord-924a8fc8d96b4eabb3a9c07ecd0fdbce
Source dataset
uspto-grants-1990_05
Patent number
US04921530

Reaction notes

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