Ethylamine → HCID 70896142, compound

HRID 2403678Notes

Reaction equation

HRID 2403678 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[C:11]([OH:13])=O.C(Cl)(=O)C(Cl)=O.[CH2:20]([NH2:22])[CH3:21]>ClCCl.CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[C:11]([NH:22][CH2:20][CH3:21])=[O:13]

Participants

6

Reactant 3

HCID 6341EthylamineHCID 65578Oxalyl chlorideHCID 71573585-bromo-1H-indazole-3-carboxylic Acid

Product 1

HCID 70896142HCID 70896142, compoundYield 94.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromo-1H-indazole-3-carboxylic acid (1.2 g, 5.0 mmol) in dichloromethane (20 mL) was added oxalyl chloride (1.26 g, 10 mmol) and 1 drop of N,N-dimethylformamide. The mixture was stirred at room temperature under a nitrogen atmosphere overnight. The reaction was concentrated and the residue was dissolved in dichloromethane (20 mL). Ethylamine (1.1 g, 25 mmol) was added dropwise. The reaction was allowed to stir at room temperature for 4 hours. The reaction mixture was concentrated to provide the title compound (1.27 g). +ESI (M+H+1) 270.9.

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionthe residue was dissolved in dichloromethane (20 mL)
  3. stirringto stir at room temperature for 4 hours
  4. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-3c663db2610e49a5912c96a657107bc6
Source dataset
uspto-grants-2014_08
Patent number
US08802688B2

Reaction notes

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