Hydrazine hydrate (1:1) → 1-{[4-Iodo-2-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-amine

HRID 1946335Notes

Reaction equation

HRID 1946335 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[CH:13]=[CH:12][C:11]([N:14]3C(=O)C4C(=CC=CC=4)C3=O)=[N:10]2)=[C:4]([C:25]([F:28])([F:27])[F:26])[CH:3]=1.O.NN>C1COCC1>[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[CH:13]=[CH:12][C:11]([NH2:14])=[N:10]2)=[C:4]([C:25]([F:26])([F:28])[F:27])[CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 667708742-(1-{[4-iodo-2-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-yl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 595478541-{[4-Iodo-2-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-amineYield 49.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of crude 2-(1-{[4-iodo-2-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-yl)-1H-isoindole-1,3(2H)-dione (1.7 g, 3.42 mmol) in THF (30 ml) was added hydrazine monohydrate (0.83 ml, 17.1 mmol, Aldrich). The resulting yellow solution was stirred at ambient temperature under nitrogen for 5 h. The resulting suspension was filtered using a hydrophobic frit and the residue washed with ether (approximately 25 ml). The filterate was concentrated in vacuo and the residue loaded in dichloromethane and purified on silica 100 g using 0-100% ethyl acetate-dichloromethane+0-20% methanol (+1% Et3N). The appropriate fractions were combined and evaporated in vacuo to give the title compound as a pale yellow solid (0.624 g); LCMS: (System 4) MH+=368, tRET=2.54 min.

Workup

  1. filtrationThe resulting suspension was filtered
  2. washthe residue washed with ether (approximately 25 ml)
  3. concentrationThe filterate was concentrated in vacuo
  4. custompurified on silica 100 g
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-aa6aa104eb334a9c8f9a49eeff0a3f4a
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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