3-(Diethylamino)pyrrolidine → HCID 178463849, compound

HRID 1092139Notes

Reaction equation

HRID 1092139 reaction equation
[CH2:1]([N:3]([CH2:9][CH3:10])[CH:4]1[CH2:8][CH2:7][NH:6][CH2:5]1)[CH3:2].Cl[C:12]1[N:13]=[CH:14][C:15]([C:18]([NH:20][C:21]2[NH:22][N:23]=[C:24]([CH2:26][CH2:27][C:28]3[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[C:30]([O:36][CH3:37])[CH:29]=3)[CH:25]=2)=[O:19])=[N:16][CH:17]=1>CS(C)=O.CO>[CH2:1]([N:3]([CH2:9][CH3:10])[CH:4]1[CH2:8][CH2:7][N:6]([C:12]2[N:13]=[CH:14][C:15]([C:18]([NH:20][C:21]3[NH:22][N:23]=[C:24]([CH2:26][CH2:27][C:28]4[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[C:30]([O:36][CH3:37])[CH:29]=4)[CH:25]=3)=[O:19])=[N:16][CH:17]=2)[CH2:5]1)[CH3:2]

Participants

5

Reactant 2

HCID 199619953-(Diethylamino)pyrrolidineHCID 178489782HCID 178489782, compound

Product 1

HCID 178463849HCID 178463849, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

N,N-diethylpyrrolidin-3-amine (142 mg, 1.00 mmol) was added to 5-chloro-N-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]pyrazine-2-carboxamide (136 mg, 0.35 mmol) in anhydrous dimethylsulfoxide (1.75 ml) at 25° C. The resulting solution was stirred at room temperature for 50 mins. The reaction mixture was diluted with methanol (5.00 ml) and the crude product was purified by ion exchange chromatography, using a SCX column. The desired product was eluted from the column using 7M NH3/MeOH and fractions were evaporated to dryness to afford impure product as a brown dry film. The crude product was purified by preparative HPLC, using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford the title compound (141 mg, 82%) as a white solid.

Workup

  1. customthe crude product was purified by ion exchange chromatography
  2. washThe desired product was eluted from the column
  3. customwere evaporated to dryness
  4. customto afford impure product as a brown dry film
  5. customThe crude product was purified by preparative HPLC
  6. additionFractions containing the desired compound
  7. customwere evaporated to dryness

Sources & evidence

ORD record
ord-f95278ee7c2841e38bf85dfba73d189a
Source dataset
uspto-grants-2012_03
Patent number
US08129391B2

Reaction notes

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