Trimethylaluminum → HCID 53846720, compound

HRID 394809Notes

Reaction equation

HRID 394809 reaction equation
C[Al](C)C.[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17](C(OC)=O)=[CH:16][C:15]([CH2:22][OH:23])=[N:14]2)=[CH:9][CH:8]=1>C(Cl)Cl.C1(C)C=CC=CC=1>[CH3:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]2[CH:17]=[CH:16][C:15]([CH2:22][OH:23])=[N:14]2)=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 16682925TrimethylaluminumHCID 54185929HCID 54185929, compound

Product 1

HCID 53846720HCID 53846720, compoundYield 176%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of of (2′-tert-butylaminosulfonyl-[1,1′]-biphen-4-yl)amine (1.44 g, 4.73 mmol) in 40 mL of methylene chloride at ambient temperature was added trimethylaluminum (14.2 mL of a 2.0 M solution in toluene, 28.4 mmol) dropwise. The resulting solution was allowed to stir until no more gas evolution was observed (˜15 min). To this solution was added 1-[(4-methoxy)phenyl]-3-(hydroxymethyl)-5-(methoxycarbonyl)pyrazole (1.24 g, 4.73 mmol) in 10 mL of methylene chloride. The resulting solution was stirred at 40° C. for 16 h and then was cooled to ambient temperature and quenched by the addition of saturated aq NH4Cl. After diluting with ethyl acetate, the organic layer was washed with 10% aq HCl, saturated aq NaHCO3 and brine, dried (MgSO4), filtered through a pad of silica gel and concentrated in vacuo. The solid residue was recrystallized from hexanes/ethyl acetate to afford 1.7 g (68%) of the title compound. LRMS (ES+): 557.1 (M+Na)+.

Workup

  1. custom(˜15 min)
  2. stirringThe resulting solution was stirred at 40° C. for 16 h
  3. customquenched by the addition of saturated aq NH4Cl
  4. additionAfter diluting with ethyl acetate
  5. washthe organic layer was washed with 10% aq HCl, saturated aq NaHCO3 and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered through a pad of silica gel
  8. concentrationconcentrated in vacuo
  9. customThe solid residue was recrystallized from hexanes/ethyl acetate

Sources & evidence

ORD record
ord-7dd6814b0f4e409ea23b177dbc1a503b
Source dataset
uspto-grants-2003_08
Patent number
US06602895B2

Reaction notes

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