1-Methylpiperazine → HCID 82891826, compound

HRID 1480816Notes

Reaction equation

HRID 1480816 reaction equation
CC1C=CC(S(O[CH2:12][CH2:13][N:14]2[CH:18]=[C:17]([I:19])[CH:16]=[N:15]2)(=O)=O)=CC=1.[CH3:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>C(#N)C>[I:19][C:17]1[CH:16]=[N:15][N:14]([CH2:13][CH2:12][N:24]2[CH2:25][CH2:26][N:21]([CH3:20])[CH2:22][CH2:23]2)[CH:18]=1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 89996125HCID 89996125, compound

Product 1

HCID 82891826HCID 82891826, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-(4-iodo-1H-pyrazol-1-yl)ethyl 4-methylbenzenesulfonate (Preparation 58, 377 mg, 0.961 mmol) in acetonitrile (6 mL) was treated with 1-methylpiperazine (1.1 mL, 9.88 mmol). The resulting mixture was stirred at room temperature for 3 days. The majority of the solvent was removed under reduced pressure and the residue partitioned between saturated aqueous NaHCO3 and EtOAc. The aqueous layer was extracted with EtOAc twice and the combined organic layers washed with water, brine, dried and concentrated. The residue was purified by silica gel column chromatography eluting with 0 to 15% MeOH in DCM to give the title compound (208 mg, 68%).

Workup

  1. customThe majority of the solvent was removed under reduced pressure
  2. customthe residue partitioned between saturated aqueous NaHCO3 and EtOAc
  3. extractionThe aqueous layer was extracted with EtOAc twice
  4. washthe combined organic layers washed with water, brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography
  8. washeluting with 0 to 15% MeOH in DCM

Sources & evidence

ORD record
ord-6f6f96f87b95481590bb07db4de81773
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

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