Ethylenediamine → HCID 86723039, compound

HRID 522325Notes

Reaction equation

HRID 522325 reaction equation
[Cl:1][C:2]1[C:3]([C:29]#[N:30])=[N:4][N:5]([CH:8]2[CH2:12][CH2:11][N:10]([C:13]3[CH:14]=[N:15][N:16]([C:21]4[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=4)[C:17]=3[CH:18]([CH3:20])[CH3:19])[C:9]2=[O:28])[C:6]=1[CH3:7].[CH2:31](N)[CH2:32][NH2:33]>CC(O)=O.CCO>[Cl:1][C:2]1[C:3]([C:29]2[NH:33][CH2:32][CH2:31][N:30]=2)=[N:4][N:5]([CH:8]2[CH2:12][CH2:11][N:10]([C:13]3[CH:14]=[N:15][N:16]([C:21]4[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=4)[C:17]=3[CH:18]([CH3:20])[CH3:19])[C:9]2=[O:28])[C:6]=1[CH3:7]

Participants

5

Reactant 2

HCID 3301EthylenediamineHCID 86723037HCID 86723037, compound

Product 1

HCID 86723039HCID 86723039, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-chloro-1-[1-[1-(4-fluorophenyl)-5-isopropylpyrazol-4-yl]-2-oxo-pyrrolidin-3-yl]-5-methylpyrazole-3-carbonitrile (0.042 g, 0.10 mmol) in ethane-1,2-diamine (1.5 mL), HOAc (0.23 mL) and EtOH (1.25 mL) was stirred at 100° C. for 2.5 hrs. The mixture was then cooled to room temperature, quenched with sat. aq. NaHCO3 (50 mL), and extracted with EtOAc (100 mL). The organic layer was separated, dried over anhydrous sodium sulfate and concentrated in vacuo to afford 3-[4-chloro-3-(4,5-dihydro-1H-imidazol-2-yl)-5-methylpyrazol-1-yl]-1-[1-(4-fluorophenyl)-5-isopropylpyrazol-4-yl]pyrrolidin-2-one (0.041 g, 87%).

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. customquenched with sat. aq. NaHCO3 (50 mL)
  3. extractionextracted with EtOAc (100 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ac9e3465f04c49908c576bb3ef32ff2f
Source dataset
uspto-grants-2016_05
Patent number
US09328116B2

Reaction notes

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