Hydrochloric Acid → HCID 14013845, compound

HRID 1649694Notes

Reaction equation

HRID 1649694 reaction equation
Cl[C:2]([F:32])([F:31])[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]([NH:18]CC2C=CC=CC=2)[C:4]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27].C(N(CC)CC)C.Cl>C(O)C.[Pd]>[F:32][CH:2]([F:31])[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]([NH2:18])[C:4]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 14013844HCID 14013844, compound

Product 1

HCID 14013845HCID 14013845, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 340 g (0.722 mol) of product from Example 99, 87.67 g (0.866 mol) of triethylamine and 10.00 g of 5% Pd/C (50% water coated) in 700 ml of ethanol was hydrogenated at 50° C. under 446 kPa of H2 pressure for 18 hours. Then 150 ml of 18% HCl (0.722 mol) was added, and the mixture was hydrogenated at 50° C. under 446 of H2 pressure for 2 hours. The reaction mixture was filtered through celite, and concentrated in vacuo to remove the ethanol. The residue was taken up in H2O, and extracted with diethyl ether. The ether phase was dried (MgSO4) and concentrated in vacuo to 161.7 g (65%) of a brown oil, 90% pure by GC analysis. Then 5.0 g were purified by HPLC in 5% ethyl acetate/cyclohexane affording 3.9 g of product as a yellow solid; mp 29°-30° C.

Workup

  1. waitthe mixture was hydrogenated at 50° C. under 446 of H2 pressure for 2 hours
  2. filtrationThe reaction mixture was filtered through celite
  3. concentrationconcentrated in vacuo
  4. customto remove the ethanol
  5. extractionextracted with diethyl ether
  6. dry with materialThe ether phase was dried (MgSO4)
  7. concentrationconcentrated in vacuo to 161.7 g (65%) of a brown oil, 90% pure by GC analysis
  8. customThen 5.0 g were purified by HPLC in 5% ethyl acetate/cyclohexane affording 3.9 g of product as a yellow solid

Sources & evidence

ORD record
ord-9d127bda964d4d78bb3baaa11c07aa3a
Source dataset
uspto-grants-1990_05
Patent number
US04921530

Reaction notes

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