Triethylamine → (4-Fluoro-3-trifluoromethylphenyl)-(4-hydrazino-[1,3,5]triazin-2-yl)-amine

HRID 563854Notes

Reaction equation

HRID 563854 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][NH2:9])[N:5]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[C:13]([C:18]([F:21])([F:20])[F:19])[CH:12]=2)[N:3]=1.C(N(CC)CC)C>[Pd].CO>[F:17][C:14]1[CH:15]=[CH:16][C:11]([NH:10][C:4]2[N:5]=[C:6]([NH:8][NH2:9])[N:7]=[CH:2][N:3]=2)=[CH:12][C:13]=1[C:18]([F:19])([F:20])[F:21]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 57507192(4-Chloro-6-hydrazino-[1,3,5]triazin-2-yl)-(4-fluoro-3-trifluoromethylphenyl)-amine

Product 1

HCID 57507193(4-Fluoro-3-trifluoromethylphenyl)-(4-hydrazino-[1,3,5]triazin-2-yl)-amineYield 48%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of compound XXII (1.5 g, 0.005 mol), triethylamine (1.41 g, 0.014 mol) and palladium on carbon (10% w/w) (0.45 g) in methanol (100 mL) was purged with nitrogen, and then shaken in a Par apparatus under an atmosphere of hydrogen gas (45 psi pressure) for 3 days. The mixture was purged with nitrogen, concentrated in vacuo to a volume of ca. 20 mL, diluted with water (50 mL) and ethyl acetate (100 mL). The biphasic mixture was filtered to remove the catalyst and the organic phase separated, rinsed with brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to afford the titled compound XXIII as a white solid (0.64 g, 48% yield, crude): m.p. 181-182° C.; ESI/MS 289 (M+H) 287 (M−H).

Workup

  1. customwas purged with nitrogen
  2. customThe mixture was purged with nitrogen
  3. concentrationconcentrated in vacuo to a volume of ca. 20 mL
  4. additiondiluted with water (50 mL) and ethyl acetate (100 mL)
  5. filtrationThe biphasic mixture was filtered
  6. customto remove the catalyst
  7. customthe organic phase separated
  8. washrinsed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4d60c333ef014ecab203ec67a311abb0
Source dataset
uspto-grants-2011_11
Patent number
US08067588B2

Reaction notes

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