Diisopropylethylamine → 3,6-dichloro-N-(2,3-difluorobenzyl)-1,2,4-triazin-5-amine

HRID 577426Notes

Reaction equation

HRID 577426 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:9])=[C:6](Cl)[N:7]=1.[F:10][C:11]1[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:12]=1[CH2:13][NH2:14].CCN(C(C)C)C(C)C>CN1C(=O)CCC1.CCOC(C)=O>[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:9])=[C:6]([NH:14][CH2:13][C:12]2[CH:15]=[CH:16][CH:17]=[C:18]([F:19])[C:11]=2[F:10])[N:7]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 27369412,3-DifluorobenzylamineHCID 122624033,5,6-Trichloro-1,2,4-triazine

Product 1

HCID 867064193,6-dichloro-N-(2,3-difluorobenzyl)-1,2,4-triazin-5-amine

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

3,5,6-Trichloro-1,2,4-triazine (520 mg, 2.8 mmol) was dissolved in 5 mL NMP. To it was added 2,3-difluorobenzylamine (0.36 mL, 3.1 mmol) and DIEA (0.54 mL, 3.1 mmol). The mixture was stirred at RT for 20 m. It was diluted with EtOAc, washed with brine twice, dried over MgSO4, concentrated in vacuo, and subjected to flash column to afford 3,6-dichloro-N-(2,3-difluorobenzyl)-1,2,4-triazin-5-amine.

Workup

  1. washwashed with brine twice
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f8ebd8b6dd44423b9befa333174a86eb
Source dataset
uspto-grants-2015_05
Patent number
US09040530B2

Reaction notes

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