Trimethylaluminum → HCID 178462529, compound

HRID 1092140Notes

Reaction equation

HRID 1092140 reaction equation
C[Al](C)C.[CH2:5]([N:7]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19]C)=O)=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)[CH3:6].[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH2:33][CH2:34][C:35]2[CH:36]=[C:37]([NH2:40])[NH:38][N:39]=2)[CH:28]=[C:29]([O:31][CH3:32])[CH:30]=1>C1(C)C=CC=CC=1>[CH3:32][O:31][C:29]1[CH:28]=[C:27]([CH2:33][CH2:34][C:35]2[CH:36]=[C:37]([NH:40][C:17](=[O:19])[C:16]3[CH:15]=[CH:14][C:13]([CH:10]4[CH2:9][CH2:8][N:7]([CH2:5][CH3:6])[CH2:12][CH2:11]4)=[CH:22][CH:21]=3)[NH:38][N:39]=2)[CH:26]=[C:25]([O:24][CH3:23])[CH:30]=1

Participants

5

Reactant 3

HCID 16682925TrimethylaluminumHCID 66589801HCID 66589801, compoundHCID 178489815HCID 178489815, compound

Product 1

HCID 178462529HCID 178462529, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
60 °C

Procedure

A 2M solution of trimethylaluminium in toluene (0.413 mL, 0.83 mmol), was added drop-wise to a suspension of methyl 4-(1-ethylpiperidin-4-yl)benzoate (0.082 g, 0.33 mmol) and 5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-amine (0.082 g, 0.33 mmol) in toluene (2 mL) at room temperature. The solution was then heated at 60° C. for 18 h. The reaction mixture was cooled, quenched with methanol (2 ml) and 2N hydrochloric acid (1 ml). The reaction mixture was purified by ion exchange chromatography, using a SCX column. The desired product was eluted from the column using 7M NH3/MeOH and fractions were evaporated to dryness. The crude product was purified by preparative HPLC, using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford the title compound (0.058 g, 38.0%) as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customquenched with methanol (2 ml) and 2N hydrochloric acid (1 ml)
  3. customThe reaction mixture was purified by ion exchange chromatography
  4. washThe desired product was eluted from the column
  5. customwere evaporated to dryness
  6. customThe crude product was purified by preparative HPLC
  7. additionFractions containing the desired compound
  8. customwere evaporated to dryness

Sources & evidence

ORD record
ord-87e5d4af5d1d4b92b63b7e8cb4a1347f
Source dataset
uspto-grants-2012_03
Patent number
US08129391B2

Reaction notes

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