1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 5-({2-[4-(2-tert-butylphenyl)piperazin-1-yl]-2-oxoethyl}sulfanyl)-1,3-dimethyl-1H-pyrazole-4-carbaldehyde

HRID 534876Notes

Reaction equation

HRID 534876 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].[CH:19]([C:21]1[C:22]([CH3:32])=[N:23][N:24]([CH3:31])[C:25]=1[S:26][CH2:27][C:28](O)=[O:29])=[O:20].Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1>O.CN(C)C=O.C(N(CC)CC)C>[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][N:16]([C:28](=[O:29])[CH2:27][S:26][C:25]2[N:24]([CH3:31])[N:23]=[C:22]([CH3:32])[C:21]=2[CH:19]=[O:20])[CH2:15][CH2:14]1)([CH3:6])([CH3:4])[CH3:5]

Participants

8

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 470023932-[(4-formyl-1,3-dimethyl-1H-pyrazol-5-yl)sulfanyl]acetic acidHCID 667511491-(2-Tert-butylphenyl)piperazine dihydrochloride

Product 1

HCID 866633985-({2-[4-(2-tert-butylphenyl)piperazin-1-yl]-2-oxoethyl}sulfanyl)-1,3-dimethyl-1H-pyrazole-4-carbaldehydeYield 64%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 1-(2-tert-butylphenyl)piperazine dihydrochloride obtained in Reference Example 1 (1.0 g), [(4-formyl-1,3-dimethyl-1H-pyrazol-5-yl)sulfanyl]acetic acid obtained in Reference Example 3 (736 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (786 mg), 1-hydroxy-1H-benzotriazole monohydrate (628 mg), triethylamine (1.39 mL), and N,N-dimethylformamide (50 mL) was stirred at room temperature for over-night. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by flash column chromatography (silica gel, 80:20-30:70 hexane/ethyl acetate) to provide 5-({2-[4-(2-tert-butylphenyl)piperazin-1-yl]-2-oxoethyl}sulfanyl)-1,3-dimethyl-1H-pyrazole-4-carbaldehyde (900 mg, 64%) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by flash column chromatography (silica gel, 80:20-30:70 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-336bfa2e363c4b49b742b8062c47e5a5
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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