Trimethylaluminum → HCID 178489760, compound

HRID 1092118Notes

Reaction equation

HRID 1092118 reaction equation
[N:1]1([C:8]2[CH:18]=[CH:17][C:11]([C:12]([O:14]CC)=O)=[CH:10][CH:9]=2)[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH2:29][CH2:30][C:31]2[CH:32]=[C:33]([NH2:36])[NH:34][N:35]=2)[CH:24]=[C:25]([O:27][CH3:28])[CH:26]=1.C[Al](C)C>C1(C)C=CC=CC=1>[N:1]1([C:8]2[CH:9]=[CH:10][C:11]([C:12]([NH:36][C:33]3[NH:34][N:35]=[C:31]([CH2:30][CH2:29][C:23]4[CH:24]=[C:25]([O:27][CH3:28])[CH:26]=[C:21]([O:20][CH3:19])[CH:22]=4)[CH:32]=3)=[O:14])=[CH:17][CH:18]=2)[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 16682925TrimethylaluminumHCID 18425301Ethyl 4-(1,4-diazepan-1-yl)benzoateHCID 178489815HCID 178489815, compound

Product 1

HCID 178489760HCID 178489760, compoundYield 2.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-(1,4-diazepan-1-yl)-N-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]benzamide was prepared following the procedure as outlined for Example 99, starting from ethyl 4-(1,4-diazepan-1-yl)benzoate (0.497 g, 2 mmol) and 5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-amine (0.495 g, 2.00 mmol) and 2M trimethylaluminium (2.50 mL, 5.0 mmol) in toluene (10 ml). The crude product was purified by silica column chromatography, eluting with a gradient of 0 to 10% 2.5 M ammonia MeOH in DCM. Fractions containing the product were evaporated to dryness and further 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 (0.024 g, 2.67%) as a white solid.

Workup

  1. custom4-(1,4-diazepan-1-yl)-N-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]benzamide was prepared
  2. customThe crude product was purified by silica column chromatography
  3. washeluting with a gradient of 0 to 10% 2.5 M ammonia MeOH in DCM
  4. additionFractions containing the product
  5. customwere evaporated to dryness
  6. customfurther purified by preparative HPLC
  7. additionFractions containing the desired compound
  8. customwere evaporated to dryness

Sources & evidence

ORD record
ord-6482a8b6dcf24009bbce890ab5f5a525
Source dataset
uspto-grants-2012_03
Patent number
US08129391B2

Reaction notes

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