Diisopropylethylamine → N-(6-Chloropyridin-3-ylmethyl)-N'-(4-fluoro-3-trifluoromethyl-phenyl)-6-{N'-[1-(4-trifluoromethoxyphenyl)-methylidene]-hydrazino}-[1,3,5]triazine-2,4-diamine

HRID 563852Notes

Reaction equation

HRID 563852 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][N:9]=[CH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=2)[N:5]=[C:4]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[C:25]([C:30]([F:33])([F:32])[F:31])[CH:24]=2)[N:3]=1.C(N(C(C)C)CC)(C)C.[NH2:43][CH2:44][C:45]1[CH:46]=[N:47][C:48]([Cl:51])=[CH:49][CH:50]=1>O1CCOCC1>[Cl:51][C:48]1[N:47]=[CH:46][C:45]([CH2:44][NH:43][C:2]2[N:3]=[C:4]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([F:29])=[C:25]([C:30]([F:33])([F:32])[F:31])[CH:24]=3)[N:5]=[C:6]([NH:8][N:9]=[CH:10][C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]([F:19])([F:20])[F:21])=[CH:13][CH:12]=3)[N:7]=2)=[CH:50][CH:49]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 70209275-(Aminomethyl)-2-chloropyridineHCID 76550911(4-Chloro-6-{N'-[1-(4-trifluoromethoxyphenyl)-methylidene]-hydrazino}-[1,3,5]triazin-2-yl)-(4-fluoro-3-trifluoromethylphenyl)-amine

Product 1

HCID 74437664N-(6-Chloropyridin-3-ylmethyl)-N'-(4-fluoro-3-trifluoromethyl-phenyl)-6-{N'-[1-(4-trifluoromethoxyphenyl)-methylidene]-hydrazino}-[1,3,5]triazine-2,4-diamineYield 32%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

{4-Chloro-6-[N′-(4-trifluoromethoxybenzylidene)hydrazino]-1,3,5-triazin-2-yl}-(4-fluoro-3-trifluoromethylphenyl)amine (XXI) (2.54 g, 5.14 mmol) was dissolved in dioxane (25 mL). To this solution was added diisopropylethylamine (1.8 mL, 10.3 mL) followed by 3-aminomethyl-6-chloropyridine (0.52 mL, 5.17 mmol). The reaction was allowed to stir overnight at room temperature. The solvent was removed under vacuum and the residue dissolved in ethyl ether (40 mL). This solution was rinsed with brine, dried over magnesium sulfate, filtered and concentrated to give a dark yellow oil which was purified by column chromatography (silica, gel, hexane/EtOAc), to afford desired product 2 (0.93 g, 32% yield).

Workup

  1. customThe solvent was removed under vacuum
  2. dissolutionthe residue dissolved in ethyl ether (40 mL)
  3. washThis solution was rinsed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a dark yellow oil which
  8. customwas purified by column chromatography (silica, gel, hexane/EtOAc)

Sources & evidence

ORD record
ord-b7f9e76a6a6049c982c85dfdc54bf337
Source dataset
uspto-grants-2011_11
Patent number
US08067588B2

Reaction notes

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