Trimethylaluminum → HCID 178456261, compound

HRID 1092152Notes

Reaction equation

HRID 1092152 reaction equation
[CH2:1]([N:4]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]2[CH:21]=[CH:20][C:14]([C:15]([O:17]CC)=O)=[CH:13][CH:12]=2)[CH2:6][CH2:5]1)[CH:2]=[CH2:3].[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH2:32][CH2:33][C:34]2[CH:35]=[C:36]([NH2:39])[NH:37][N:38]=2)[CH:27]=[C:28]([O:30][CH3:31])[CH:29]=1.C[Al](C)C.C(Cl)Cl.CCOCC>C1(C)C=CC=CC=1>[CH3:31][O:30][C:28]1[CH:27]=[C:26]([CH2:32][CH2:33][C:34]2[CH:35]=[C:36]([NH:39][C:15](=[O:17])[C:14]3[CH:13]=[CH:12][C:11]([N:7]4[CH2:8][CH2:9][CH2:10][N:4]([CH2:1][CH:2]=[CH2:3])[CH2:5][CH2:6]4)=[CH:21][CH:20]=3)[NH:37][N:38]=2)[CH:25]=[C:24]([O:23][CH3:22])[CH:29]=1

Participants

6

Reactant 4

HCID 16682925TrimethylaluminumHCID 21881112Ethyl ether methylene chlorideHCID 66589947Ethyl 4-(4-allyl-1,4-diazepan-1-yl)benzoateHCID 178489815HCID 178489815, compound

Product 1

HCID 178456261HCID 178456261, compoundYield 14.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]-4-(4-prop-2-enyl-1,4-diazepan-1-yl)benzamide was prepared using the same procedure as for Example 159, but starting from ethyl 4-(4-allyl-1,4-diazepan-1-yl)benzoate (0.288 g, 1 mmol, 5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-amine (0.247 g, 1 mmol) and a 2M solution of trimethylaluminium (1.250 mL, 2.50 mmol) in toluene. 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 a gum, which solidified on trituration with DCM/Ether to afford the title compound (0.071 g, 14.50%).

Workup

  1. customN-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]-4-(4-prop-2-enyl-1,4-diazepan-1-yl)benzamide was prepared
  2. customThe crude product was purified by preparative HPLC
  3. additionFractions containing the desired compound
  4. customwere evaporated to dryness
  5. customto afford a gum, which

Sources & evidence

ORD record
ord-45bee38e1bf642e5b95c3f32d4bcb6df
Source dataset
uspto-grants-2012_03
Patent number
US08129391B2

Reaction notes

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