HCID 86760776, compound → HCID 69224309, compound

HRID 2374100Notes

Reaction equation

HRID 2374100 reaction equation
[ClH:1].[N:2]([C:4]1[CH:8]=[N:7][N:6]([CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[C:5]=1[NH2:16])=O.[H][H]>C(O)C.[Pd]>[ClH:1].[ClH:1].[ClH:1].[N:13]1[CH:14]=[CH:15][C:10]([CH2:9][N:6]2[C:5]([NH2:16])=[C:4]([NH2:2])[CH:8]=[N:7]2)=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 86760776HCID 86760776, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69224309HCID 69224309, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In an autoclave, 38.1 g (158 mmol) of the crude product from Step 2.2 was suspended in 800 mL of ethanol and hydrogenated at 9 bar of hydrogen pressure for 2 hours using 3.8 g of Pd/C (10%). The catalyst was then filtered off through diatomaceous earth, to the filtrate was added 200 mL of 3M ethanolic hydrochloric acid, and the solution was concentrated to incipient crystallization in a rotary evaporator at 40° C. To complete the crystallization, the mixture was cooled in an ice bath, after which the solid was filtered off. The product was then washed with a small amount of ethyl acetate and dried at 40° C. under vacuum. This gave 19.5 g (41% of the theoretical) of a slightly pink-colored powder.

Workup

  1. filtrationThe catalyst was then filtered off through diatomaceous earth, to the filtrate
  2. additionwas added 200 mL of 3M ethanolic hydrochloric acid
  3. concentrationthe solution was concentrated to incipient crystallization in a rotary evaporator at 40° C
  4. customthe crystallization
  5. temperaturethe mixture was cooled in an ice bath
  6. filtrationafter which the solid was filtered off
  7. washThe product was then washed with a small amount of ethyl acetate
  8. customdried at 40° C. under vacuum

Sources & evidence

ORD record
ord-92329031e49849ef8d4e77e7f6000fc4
Source dataset
uspto-grants-2008_12
Patent number
US07462204B2

Reaction notes

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