Triethylamine → 1-{[5-(Benzyloxy)-1-methyl-1H-pyrazol-3-yl]carbonyl}-4-(2-tert-butylphenyl)piperazine

HRID 535010Notes

Reaction equation

HRID 535010 reaction equation
Cl.Cl.[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)([CH3:6])([CH3:5])[CH3:4].[CH2:19]([O:26][C:27]1[N:31]([CH3:32])[N:30]=[C:29]([C:33](O)=[O:34])[CH:28]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(CC)CC)C.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O.O>[CH2:19]([O:26][C:27]1[N:31]([CH3:32])[N:30]=[C:29]([C:33]([N:16]2[CH2:17][CH2:18][N:13]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[C:3]([CH3:6])([CH3:4])[CH3:5])[CH2:14][CH2:15]2)=[O:34])[CH:28]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 667511491-(2-Tert-butylphenyl)piperazine dihydrochlorideHCID 667513585-(Benzyloxy)-1-methyl-1H-pyrazole-3-carboxylic acid

Product 1

HCID 667928171-{[5-(Benzyloxy)-1-methyl-1H-pyrazol-3-yl]carbonyl}-4-(2-tert-butylphenyl)piperazine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(2-tert-butylphenyl)piperazine dihydrochloride obtained in Reference Example 1 (1.0 g, 3.4 mmol), 5-(benzyloxy)-1-methyl-1H-pyrazole-3-carboxylic acid (0.975 g, 4.2 mmol), triethylamine (1.39 mL, 10.0 mmol), EDCI (0.978 g, 5.1 mmol) and HOBt (0.781 g, 5.1 mmol) in N,N-dimethylformamide (10 mL) was stirred at room temperature for 16 h. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to purify the residue by NH-silica gel column chromatography (hexane/ethyl acetate 90:10 to 0:100). Solvent was removed to obtain a solid (1.75 g, quant.).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto purify the residue by NH-silica gel column chromatography (hexane/ethyl acetate 90:10 to 0:100)
  7. customSolvent was removed
  8. customto obtain a solid (1.75 g, quant.)

Sources & evidence

ORD record
ord-f7117ff894304c12a1ae73fb9d2bbaac
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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