Trimethylaluminum → HCID 178462579, compound

HRID 1911467Notes

Reaction equation

HRID 1911467 reaction equation
[CH2:1]([N:3]1[CH2:9][CH2:8][CH2:7][N:6]([C:10]2[CH:20]=[CH:19][C:13]([C:14]([O:16]CC)=O)=[CH:12][CH:11]=2)[CH2:5][CH2:4]1)[CH3:2].[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH2:31][CH2:32][C:33]2[CH:34]=[C:35]([NH2:38])[NH:36][N:37]=2)[CH:26]=[C:27]([O:29][CH3:30])[CH:28]=1.C[Al](C)C.C(Cl)Cl.CCOCC>C1(C)C=CC=CC=1>[CH3:30][O:29][C:27]1[CH:26]=[C:25]([CH2:31][CH2:32][C:33]2[CH:34]=[C:35]([NH:38][C:14](=[O:16])[C:13]3[CH:12]=[CH:11][C:10]([N:6]4[CH2:7][CH2:8][CH2:9][N:3]([CH2:1][CH3:2])[CH2:4][CH2:5]4)=[CH:20][CH:19]=3)[NH:36][N:37]=2)[CH:24]=[C:23]([O:22][CH3:21])[CH:28]=1

Participants

6

Reactant 4

HCID 16682925TrimethylaluminumHCID 21881112Ethyl ether methylene chlorideHCID 66589981Ethyl 4-(4-ethyl-1,4-diazepan-1-yl)benzoateHCID 178489815HCID 178489815, compound

Product 1

HCID 178462579HCID 178462579, compoundYield 25.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]-4-(4-ethyl-1,4-diazepan-1-yl)benzamide was prepared using the same procedure as for Example 159, but starting from ethyl 4-(4-ethyl-1,4-diazepan-1-yl)benzoate (0.502 g, 1.4 mmol), 5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-amine (0.346 g, 1.40 mmol) and A 2M solution of trimethylaluminium (1.750 mL, 3.50 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 (0.171 g, 25.6%) as a white solid.

Workup

  1. customN-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]-4-(4-ethyl-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-0808319dc4df469485d4ff07dca56d08
Source dataset
uspto-grants-2013_12
Patent number
US08604022B2

Reaction notes

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