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

HRID 1911394Notes

Reaction equation

HRID 1911394 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-5e18f8e8324246d0853641dcf3eadb10
Source dataset
uspto-grants-2013_12
Patent number
US08604022B2

Reaction notes

Loading…