HCID 22258787, compound → HCID 135550591, compound

HRID 412295Notes

Reaction equation

HRID 412295 reaction equation
[NH2:1][C:2]1[C:7]([CH2:8][N:9]=[N+]=[N-])=[C:6]([CH:12]2[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13]2)[CH:5]=[C:4]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[O:31]CC2C=CC=CC=2)[N:3]=1>C(OCC)(=O)C.[Pd]>[NH2:1][C:2]1[C:7]([CH2:8][NH2:9])=[C:6]([CH:12]2[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13]2)[CH:5]=[C:4]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[OH:31])[N:3]=1

Participants

4

Reactant 1

HCID 22258787HCID 22258787, compound

Product 1

HCID 135550591HCID 135550591, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of tert-butyl 3-{2-amino-3-(azidomethyl)-6-[2-(benzyloxy)phenyl]-4-pyridinyl}-1-piperidinecarboxylate (0.030 g, 0.058 mmol) in ethyl acetate (1.0 mL) was hydrogenated at 1 atm in the presence of palladium on charcoal (10%, 0.015 g) overnight. The resulting mixture was filtered and washed with ethyl acetate. The combined filtrate was concentrated under reduced pressure to give tert-butyl 3-[2-amino-3-(aminomethyl)-6-(2-hydroxyphenyl)-4-pyridinyl]-1-piperidinecarboxylate, which was used for the next step without further purification.

Workup

  1. filtrationThe resulting mixture was filtered
  2. washwashed with ethyl acetate
  3. concentrationThe combined filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-048959430a9a4c0b962c9fc30359bf55
Source dataset
uspto-grants-2003_05
Patent number
US06562811B1

Reaction notes

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