Hydrazine hydrate (1:1) → N-(6-Chloro-pyridin-3-ylmethyl)-N'-(4-fluoro-3-trifluoromethylphenyl)-6-hydrazino-[1,3,5]triazine-2,4-diamine

HRID 1931195Notes

Reaction equation

HRID 1931195 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:11]=[N:12][C:13]([Cl:16])=[CH:14][CH:15]=2)[N:5]=[C:4]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[C:20]([C:25]([F:28])([F:27])[F:26])[CH:19]=2)[N:3]=1.O.[NH2:30][NH2:31]>O1CCOCC1.O>[Cl:16][C:13]1[N:12]=[CH:11][C:10]([CH2:9][NH:8][C:6]2[N:5]=[C:4]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[C:20]([C:25]([F:28])([F:27])[F:26])[CH:19]=3)[N:3]=[C:2]([NH:30][NH2:31])[N:7]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 575071896-Chloro-N-(6-chloropyridin-3-ylmethyl)-N'-(4-fluoro-3-trifluoromethylphenyl)-1,3,5-triazine-2,4-diamine

Product 1

HCID 57507190N-(6-Chloro-pyridin-3-ylmethyl)-N'-(4-fluoro-3-trifluoromethylphenyl)-6-hydrazino-[1,3,5]triazine-2,4-diamineYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 6-Chloro-N-(6-chloropyridin-3-ylmethyl)-N′-(4-fluoro-3-trifluoromethylphenyl)-[1,3,5]triazine-2,4-diamine (XVIII) (3.0 g, 6.9 mmol) in dioxane (30 mL) was added hydrazine hydrate (2 mL), and the mixture stirred at ambient temperature for 30 min. The mixture was diluted with water, the resulting slurry stirred for 10 min and filtered under vacuum to give a white solid. This solid was washed with water and dried under vacuum to give N-(6-chloro-pyridin-3-ylmethyl)-N′-(4-fluoro-3-trifluoromethylphenyl)-6-hydrazino-1,3,5-triazine-2,4-diamine (XIX) (2.89 g, 97% yield): 1H NMR (CDCl3); δ 9.40 (m, 1H), 8.5-7.5 (m, 4H), 7.45 (m, 2H), 7.33 (m, 2H), 4.49, m, 2H), 4.17 (bs, 2H); ESI/MS 429 (M+H), 427 (M−H).

Workup

  1. stirringthe resulting slurry stirred for 10 min
  2. filtrationfiltered under vacuum
  3. customto give a white solid
  4. washThis solid was washed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-6aa2750793194d27bf26d8fb06f75bd6
Source dataset
uspto-grants-2012_05
Patent number
US08188273B2

Reaction notes

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