Triethylamine → HCID 58076147, compound

HRID 1747714Notes

Reaction equation

HRID 1747714 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[F:18])=[N:9][CH:10]=2)[N:7]=1.C(N(CC)CC)C.[H][H]>[Pd].C(OCC)(=O)C>[F:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH2:11][C:8]1[N:6]2[N:7]=[CH:2][CH:3]=[CH:4][C:5]2=[CH:10][N:9]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 86716489HCID 86716489, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 58076147HCID 58076147, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2.004 g of palladium on carbon (5%) were initially charged under argon, and 20.04 g (76.58 mmol) of the compound obtained in Example 3A in ethyl acetate (750 ml) were then added. 21.348 ml (153.159 mmol) of triethylamine were then added, and the reaction mixture was hydrogenated at standard hydrogen pressure and 20° C. for 16 hours. The same amount of catalyst as indicated above was then added, and the reaction mixture was hydrogenated at standard hydrogen pressure and 20° C. for another night. The mixture was then filtered through Celite, the filter cake was washed with ethanol and the filtrate was concentrated and dried under high vacuum. This gave 22.79 g of the target compound (about 100% of theory, contaminated with triethylamine).

Workup

  1. additionabove was then added
  2. filtrationThe mixture was then filtered through Celite
  3. washthe filter cake was washed with ethanol
  4. concentrationthe filtrate was concentrated
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-90f749892b554113973f43cbab6b9c67
Source dataset
uspto-grants-2015_10
Patent number
US09150580B2

Reaction notes

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