Diisopropylethylamine → HCID 178489777, compound

HRID 16838

Reaction equation

HRID 16838 reaction equation
Cl.Cl.[N:3]1([CH:9]([CH3:12])[CH2:10][OH:11])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.C(N(C(C)C)C(C)C)C.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH2:32][CH2:33][C:34]2[CH:35]=[C:36]([NH:39][C:40](=[O:48])[C:41]3[CH:46]=[CH:45][C:44](F)=[CH:43][CH:42]=3)[NH:37][N:38]=2)[CH:27]=[C:28]([O:30][CH3:31])[CH:29]=1>CS(C)=O>[CH3:31][O:30][C:28]1[CH:27]=[C:26]([CH2:32][CH2:33][C:34]2[CH:35]=[C:36]([NH:39][C:40](=[O:48])[C:41]3[CH:42]=[CH:43][C:44]([N:6]4[CH2:7][CH2:8][N:3]([CH:9]([CH3:12])[CH2:10][OH:11])[CH2:4][CH2:5]4)=[CH:45][CH:46]=3)[NH:37][N:38]=2)[CH:25]=[C:24]([O:23][CH3:22])[CH:29]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 119720442-(Piperazin-1-yl)propan-1-ol dihydrochlorideHCID 178489757HCID 178489757, compound

Product 1

HCID 178489777HCID 178489777, compoundYield 15.44%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-(Piperazin-1-yl)propan-1-ol 2HCl (0.274 g, 1.26 mmol) was added to N-ethyl-N-propan-2-ylpropan-2-amine (0.330 mL, 1.89 mmol) in DMSO (5 mL). The reaction mixture was stirred at room temperature for 10 mins. N-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]-4-fluorobenzamide (0.233 g, 0.63 mmol) was added and the mixture heated at 110° C. for 18 h under nitrogen. Heating was continued for 12 additional days. The reaction was cooled and the crude mixture was purified by ion exchange chromatography, using a SCX column. The desired product was eluted from the column using 7M NH3/MeOH and pure fractions were evaporated to dryness to afford crude product. 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 (0.048 g, 15.44%) as a cream solid.

Workup

  1. temperaturethe mixture heated at 110° C. for 18 h under nitrogen
  2. temperatureHeating
  3. temperatureThe reaction was cooled
  4. customthe crude mixture was purified by ion exchange chromatography
  5. washThe desired product was eluted from the column
  6. customwere evaporated to dryness
  7. customto afford crude product
  8. customThe crude product was purified by preparative HPLC
  9. additionFractions containing the desired compound
  10. customwere evaporated to dryness

Sources & evidence

ORD record
ord-5564cb277b7047dcbcc28fe5f170e378
Source dataset
uspto-grants-2010_06
Patent number
US07737149B2

Linked notes

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