Dimethylpiperazine → HCID 178489806, compound

HRID 1911399Notes

Reaction equation

HRID 1911399 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]([C:8]([NH:10][C:11]2[NH:12][N:13]=[C:14]([CH2:16][CH2:17][C:18]3[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20]([O:26][CH3:27])[CH:19]=3)[CH:15]=2)=[O:9])=[N:6][CH:7]=1.[CH3:28][N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH:30]1[CH3:35]>CS(C)=O>[CH3:27][O:26][C:20]1[CH:19]=[C:18]([CH2:17][CH2:16][C:14]2[CH:15]=[C:11]([NH:10][C:8]([C:5]3[CH:4]=[N:3][C:2]([N:32]4[CH2:33][CH2:34][N:29]([CH3:28])[CH:30]([CH3:35])[CH2:31]4)=[CH:7][N:6]=3)=[O:9])[NH:12][N:13]=2)[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=1

Participants

4

Reactant 2

HCID 198037DimethylpiperazineHCID 178489782HCID 178489782, compound

Product 1

HCID 178489806HCID 178489806, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5-Chloro-N-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]pyrazine-2-carboxamide (388 mg, 1.00 mmol) was added in one portion to 1,2-dimethyl-piperazine (228 mg, 2.00 mmol) in anhydrous dimethylsulfoxide (2.00 ml) at 25° C. The resulting solution was stirred at ambient temperature for 2 h. The residue was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3/MeOH to afford impure material. The concentrated eluent was purified by silica column chromatography, eluting with a gradient of 0 to 10% 7M NH3/MeOH in DCM. Pure fractions were evaporated to dryness to afford the title compound (375 mg, 81%) as a yellow solid.

Workup

  1. customThe residue was purified by ion exchange chromatography
  2. washThe desired product was eluted from the column
  3. customto afford impure material
  4. customThe concentrated eluent was purified by silica column chromatography
  5. washeluting with a gradient of 0 to 10% 7M NH3/MeOH in DCM
  6. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-aa0757147bb24af68be15b73a6070126
Source dataset
uspto-grants-2013_12
Patent number
US08604022B2

Reaction notes

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