HCID 57590905, compound → HCID 57590907, compound

HRID 1783760Notes

Reaction equation

HRID 1783760 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][CH2:8]/[CH:9]=[CH:10]/[C:11]1[C:20]2[C:15](=[CH:16][C:17]([Cl:21])=[CH:18][CH:19]=2)[C:14]2=[N:22][NH:23][C:24](=[O:25])[N:13]2[CH:12]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>CCO.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6](=[O:26])[NH:7][CH2:8][CH2:9][CH2:10][C:11]1[C:20]2[C:15](=[CH:16][C:17]([Cl:21])=[CH:18][CH:19]=2)[C:14]2=[N:22][NH:23][C:24](=[O:25])[N:13]2[CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 57590905HCID 57590905, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57590907HCID 57590907, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of tert-butyl[(2E)-3-(9-chloro-3-oxo-2,3-dihydro[1,2,4]triazolo[3,4-a]isoquinolin-6-yl)prop-2-en-1-yl]carbamate (3-10)(14 mg, 0.037 mmol, 1.0 equiv.) in EtOH (4 mL), was added Pd(OH)2/C (20% Pd, 1.3 mg, 0.002 mmol, 0.05 equiv.). The reaction mixture was stirred at room temperature for 1.5 hours under atmospheric pressure of hydrogen. The catalyst was then filtered off, and the filtrate was concentrated to dryness. The resulting crude product was purified with reverse phase HPLC (H2O/CH3CN gradient w/0.1% TFA) to afford the titled product (3-12). LRMS m/z (M+H) 377.1 found, 377.1 required.

Workup

  1. filtrationThe catalyst was then filtered off
  2. concentrationthe filtrate was concentrated to dryness
  3. customThe resulting crude product was purified with reverse phase HPLC (H2O/CH3CN gradient w/0.1% TFA)

Sources & evidence

ORD record
ord-921ff8c7e2ab4625894cbbacc16e798f
Source dataset
uspto-grants-2009_03
Patent number
US07501435B2

Reaction notes

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