Hydrazinecarboxylic acid, ethyl ester → HCID 57590926, compound

HRID 1783754Notes

Reaction equation

HRID 1783754 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2Cl)=[CH:4][CH:3]=1.[C:13](OCC)(=[O:16])[NH:14][NH2:15]>CCO>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]3[C:13](=[O:16])[NH:14][N:15]=[C:9]32)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 65020247-Bromo-1-Chloroisoquinoline

Product 1

HCID 57590926HCID 57590926, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7-Bromo-1-chloroisoquinoline (1-1) (79 mg, 0.327 mmol, 1.0 equiv) and Ethyl carbazate (34 mg, 0.33 mmol, 1.0 equiv) were suspended in EtOH (1.5 mL). The reaction mixture was irradiated in microwave at 170° C. for 40 minutes. The crude mixture was purified with reverse phase HPLC (H2O/CH3CN gradient w/0.1% TFA present) to yield 9-bromo[1,2,4]triazolo[3,4-a]isoquinolin-3(2H)-one (1-2). LRMS m/z (M+H) 263.9 and 264.9 found, 264.1 and 265.1 required.

Workup

  1. customThe reaction mixture was irradiated in microwave at 170° C. for 40 minutes
  2. customThe crude mixture was purified with reverse phase HPLC (H2O/CH3CN gradient w/0.1% TFA present)

Sources & evidence

ORD record
ord-d53a21ed7ab44bd09fe0c7f4e788d4b5
Source dataset
uspto-grants-2009_03
Patent number
US07501435B2

Reaction notes

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