Cyclopropylamine → HCID 86613235, compound

HRID 2099038Notes

Reaction equation

HRID 2099038 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19](O)=[O:20])[C:3]=1[S:22][C:23]([F:26])([F:25])[F:24].[CH:27]1([NH2:30])[CH2:29][CH2:28]1>O1CCOCC1.O>[CH:27]1([NH:30][C:19]([C:4]2[C:3]([S:22][C:23]([F:24])([F:26])[F:25])=[C:2]([NH2:1])[N:6]([C:7]3[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:15])([F:16])[F:17])=[CH:9][C:8]=3[Cl:18])[N:5]=2)=[O:20])[CH2:29][CH2:28]1

Participants

5

Reactant 2

HCID 69828CyclopropylamineHCID 226184975-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfanyl)pyrazole-3-carboxylic acid

Product 1

HCID 86613235HCID 86613235, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylthio-1H-pyrazole-3-carboxylic acid (0.85 g, 1.83 mmol) and 1,1-dicarbonylimidazole (0.36 g, 2.20 mmol) in dioxane was heated to. 55° C. for 2 hours. Cyclopropylamine (0.20 ml, 2.83 mmol) was then added and stirring continued at 55° C. for 6 hours. The cooled mixture was diluted with water, extracted with ethyl acetate, washed with aqueous potassium hydrogensulfate (5%), dried over magnesium sulfate and evaporated to give the title compound (0.762 g, yield 87%) as off-white crystals, mp 193° C., 1H NMR (CDCl3): 0.64 (m, 2H, cyclopropyl), 0.83 (m, 2H, cyclopropyl), 2,87 (m,1H, cyclopropyl), 4.31 (bs, 2H, NH2), 6.82 (bs,1 H, C(O)NH), and 7.80 (s, 2H, Ar—H).

Workup

  1. temperaturewas heated to
  2. waitcontinued at 55° C. for 6 hours
  3. extractionextracted with ethyl acetate
  4. washwashed with aqueous potassium hydrogensulfate (5%)
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-18ec271f997f4e3dbed88f19dfc3ea03
Source dataset
uspto-grants-2009_08
Patent number
US07569516B2

Reaction notes

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