Acetone → 4-(4-Cyclobutylpiperazin-1-yl)-N-[5-[(3,5-dimethoxyphenyl)methoxy]-2H-pyrazol-3-yl]benzamide

HRID 16822Notes

Reaction equation

HRID 16822 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][O:12][C:13]2[CH:14]=[C:15]([NH2:18])[NH:16][N:17]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[CH:19]1([N:23]2[CH2:28][CH2:27][N:26]([C:29]3[CH:39]=[CH:38][C:32]([C:33](OCC)=[O:34])=[CH:31][CH:30]=3)[CH2:25][CH2:24]2)[CH2:22][CH2:21][CH2:20]1.C[Al](C)C.CC(C)=O>C1(C)C=CC=CC=1.C(#N)C>[CH:19]1([N:23]2[CH2:28][CH2:27][N:26]([C:29]3[CH:39]=[CH:38][C:32]([C:33]([NH:18][C:15]4[NH:16][N:17]=[C:13]([O:12][CH2:11][C:5]5[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=5)[CH:14]=4)=[O:34])=[CH:31][CH:30]=3)[CH2:25][CH2:24]2)[CH2:20][CH2:21][CH2:22]1

Participants

7

Reactant 4

HCID 180AcetoneHCID 16682925TrimethylaluminumHCID 574403815-[(3,5-dimethoxyphenyl)methoxy]-2H-pyrazol-3-amineHCID 57440408Ethyl 4-(4-cyclobutylpiperazin-1-yl)benzoate

Product 1

HCID 665898704-(4-Cyclobutylpiperazin-1-yl)-N-[5-[(3,5-dimethoxyphenyl)methoxy]-2H-pyrazol-3-yl]benzamideYield 23.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 6342AcetonitrileSolvent

Procedure

4-(4-Cyclobutylpiperazin-1-yl)-N-[5-[(3,5-dimethoxyphenyl)methoxy]-2H-pyrazol-3-yl]benzamide was prepared following the procedure as outlined for Example 100, starting from 5-[(3,5-dimethoxyphenyl)methoxy]-2H-pyrazol-3-amine (0.173 g, 0.69 mmol), ethyl 4-(4-cyclobutylpiperazin-1-yl)benzoate (0.2 g, 0.69 mmol) and a 2M solution of trimethylaluminium in toluene (1.387 mL, 2.77 mmol) in toluene (10 ml) at room temperature for 20 h. The reaction mixture was poured into acetone (20 mL), quenched with excess damp sodium sulphite, filtered and evaporated to afford a yellow solid. Acetonitrile (10 ml) was added and this was filtered to afford the title compound (0.079 g, 23.17%) as a white solid.

Workup

  1. custom4-(4-Cyclobutylpiperazin-1-yl)-N-[5-[(3,5-dimethoxyphenyl)methoxy]-2H-pyrazol-3-yl]benzamide was prepared
  2. customquenched with excess damp sodium sulphite
  3. filtrationfiltered
  4. customevaporated
  5. customto afford a yellow solid
  6. filtrationthis was filtered

Sources & evidence

ORD record
ord-fa2a768fa3db4241a868502de7e30586
Source dataset
uspto-grants-2010_06
Patent number
US07737149B2

Reaction notes

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