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Trimethylaluminum → 3-[[1-(4-Fluorophenyl)-5-isopropylpyrazol-4-yl]amino]-3-[2-methyl-4-(trifluoromethyl)imidazol-1-yl]propan-1-ol

HRID 522317
Notes
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Reaction equation

HRID 522317 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH:13]([CH3:15])[CH3:14])=[C:11]([NH2:16])[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[CH3:17][C:18]1[N:19]([CH:27]2[CH2:31][CH2:30][O:29]C2=O)[CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[N:22]=1.C[Al](C)C>[OH-].[NH4+]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([CH:13]([CH3:14])[CH3:15])=[C:11]([NH:16][CH:27]([N:19]3[CH:20]=[C:21]([C:23]([F:25])([F:26])[F:24])[N:22]=[C:18]3[CH3:17])[CH2:31][CH2:30][OH:29])[CH:10]=[N:9]2)=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 16682925TrimethylaluminumHCID 664257241-(4-Fluorophenyl)-5-isopropyl-pyrazol-4-amineHCID 867230313-[2-Methyl-4-(trifluoromethyl)imidazol-1-yl]tetrahydrofuran-2-one

Product 1

HCID 867230303-[[1-(4-Fluorophenyl)-5-isopropylpyrazol-4-yl]amino]-3-[2-methyl-4-(trifluoromethyl)imidazol-1-yl]propan-1-olYield 24%

Reagents, catalysts & solvents 1

HCID 14923
Ammonium Hydroxide
Solvent

Conditions

Temperature
55 °C

Procedure

A mixture of 1-(4-fluorophenyl)-5-isopropyl-pyrazol-4-amine (0.070 g, 0.32 mmol), 3-[2-methyl-4-(trifluoromethyl)imidazol-1-yl]tetrahydrofuran-2-one (0.070 g, 0.30 mmol) and AlMe3 (0.50 mL, 1.0 mmol, 2 M/toluene) was heated at 55° C. for 1.5 hrs. The mixture was then cooled to room temperature, diluted with aqueous ammonium hydroxide, and extracted with EtOAc. The organic layer was separated, dried over anhydrous sodium sulfate, concentrated in vacuo, and purified by flash chromatography (SiO2, 0˜20% MeOH/CH2Cl2 gradient elution) to give 3-[[1-(4-fluorophenyl)-5-isopropylpyrazol-4-yl]amino]-3-[2-methyl-4-(trifluoromethyl)imidazol-1-yl]propan-1-ol (0.030 g, 24%).

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography (SiO2, 0˜20% MeOH/CH2Cl2 gradient elution)

Sources & evidence

ORD record
ord-d3fe0f7fe50147b5bbd43efbdbda4cba
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09328116B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes