1,2,3,4-Tetrazine → HCID 11965780, compound

HRID 1894124Notes

Reaction equation

HRID 1894124 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([C:10]#[CH:11])[C:7]([C:12]([F:15])([F:14])[F:13])=[CH:6][C:5]=1[NH2:16].[N:18]1[CH:23]=[CH:22]N=N[N:19]=1>ClCCCl>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([C:10]2[CH:22]=[CH:23][N:18]=[N:19][CH:11]=2)[C:7]([C:12]([F:13])([F:15])[F:14])=[CH:6][C:5]=1[NH2:16]

Participants

4

Reactant 2

HCID 124433661,2,3,4-TetrazineHCID 59164456HCID 59164456, compound

Product 1

HCID 11965780HCID 11965780, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 2-amino-5-ethynyl-4-trifluoromethyl-benzoic acid methyl ester (150 mg, 0.62 mmol) and tetrazine (55.7 mg, 0.68 mmol) in 1,2-dichloroethane (3 mL) in a sealed tube was heated in the microwave at 130° C. for 40 min and at 120° C. for 40 min. After cooling to r.t., the solvent was removed in vacuo. The residue was purified by flash chromatography (10 g silica gel, hexanes→EtOAc:hexanes (2:3)) to provide 2-amino-5-pyridazin-4-yl-4-trifluoromethyl-benzoic acid methyl ester (74 mg, 40%) as a solid. API-ES: m/z 298 [M+H]+, rt 3.54 min.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was purified by flash chromatography (10 g silica gel, hexanes→EtOAc:hexanes (2:3))

Sources & evidence

ORD record
ord-b200cd0cacad4b8d9d25a6b22b7138fc
Source dataset
uspto-grants-2013_08
Patent number
US08513268B2

Reaction notes

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