HCID 23292346, compound → HCID 23292352, compound

HRID 365504Notes

Reaction equation

HRID 365504 reaction equation
[NH2:1][CH2:2][C:3]([NH:16]C(C1C=CC=CC=1)C)([CH3:15])[CH2:4][CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1>C(O)(=O)C.CCO.[OH-].[OH-].[Pd+2]>[CH3:15][C:3]([NH2:16])([CH2:4][CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:2][NH2:1]

Participants

5

Reactant 1

HCID 23292346HCID 23292346, compound

Product 1

HCID 23292352HCID 23292352, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A suspension of 0.50 g (1.55 mmol) of the compound obtained in Step 3 and 0.14 g of Pd(OH)2 in a mixture of 0.8 ml of acetic acid and 50 ml of EtOH is hydrogenated at 20° C. under 1 bar for 20 hours. After filtration of the mixture and concentration in vacuo, the residue is taken up in 1N aq. NaOH (10 ml) and extracted with CH2Cl2 (3×10 ml); the combined organic phases are washed with saturated aq. NaCl, dried and concentrated to yield the title compound in the form of an oil, which is used in the following reaction without being otherwise purified.

Workup

  1. filtrationAfter filtration of the mixture and concentration in vacuo
  2. extractionextracted with CH2Cl2 (3×10 ml)
  3. washthe combined organic phases are washed with saturated aq. NaCl
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-516557d52aab4869a40feb43548fd127
Source dataset
uspto-grants-2000_10
Patent number
US06127396

Reaction notes

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