1,2,3,4-Tetrazine → HCID 59164418, compound

HRID 1894127Notes

Reaction equation

HRID 1894127 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([C:10]#[CH:11])[C:7]([CH:12]([CH3:14])[CH3:13])=[CH:6][C:5]=1[NH2:15].[N:17]1[CH:22]=[CH:21]N=N[N:18]=1>ClCCCl>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([C:10]2[CH:21]=[CH:22][N:17]=[N:18][CH:11]=2)[C:7]([CH:12]([CH3:14])[CH3:13])=[CH:6][C:5]=1[NH2:15]

Participants

4

Reactant 2

HCID 124433661,2,3,4-TetrazineHCID 59164488HCID 59164488, compound

Product 1

HCID 59164418HCID 59164418, compoundYield 26.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 2-amino-5-ethynyl-4-isopropyl-benzoic acid methyl ester (718 mg, 3.3 mmol) and tetrazine (406.8 mg, 5.0 mmol) in 1,2-dichloroethane (15 mL) in a sealed tube was heated in the microwave at 130° C. for 45 min. The reaction mixture was then concentrated in vacuo and the residue was purified by flash chromatography (50 g silica gel, hexanes→EtOAc:hexanes (1:1)) to provide the title compound (236 mg, 26%). API-ES: m/z 272 [M+H]+, rt 3.38 min.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customthe residue was purified by flash chromatography (50 g silica gel, hexanes→EtOAc:hexanes (1:1))

Sources & evidence

ORD record
ord-bc8a02edd19e4ffc9c734fc9d50aace2
Source dataset
uspto-grants-2013_08
Patent number
US08513268B2

Reaction notes

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