Triethylamine → HCID 57743080, compound

HRID 1896486Notes

Reaction equation

HRID 1896486 reaction equation
[CH:1]([CH:3]([CH2:9][N:10]1[CH2:14][CH:13]([CH2:15][CH2:16][CH3:17])[CH2:12][C:11]1=[O:18])[C:4]([O:6]CC)=O)=O.CCN(CC)CC.[C:26]1([CH2:32][NH:33][NH2:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.Cl.Cl>C1(C)C=CC=CC=1>[CH2:32]([N:33]1[C:4](=[O:6])[CH:3]([CH2:9][N:10]2[CH2:14][CH:13]([CH2:15][CH2:16][CH3:17])[CH2:12][C:11]2=[O:18])[CH:1]=[N:34]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 146540Benzylhydrazine dihydrochlorideHCID 57743091HCID 57743091, compound

Product 1

HCID 57743080HCID 57743080, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
40 °C

Procedure

In a three neck flask, fitted with a magnetic stirrer, under inert atmosphere, ethyl 2-formyl-3-(2-oxo-4-propylpyrrolidin-1-yl)propanoate x280 (0.9 g) in PhMe (10 ml) is added onto a solution of Et3N (1.6 ml) and PhCH2NHNH2.2HCl (0.75 g, 0.0039 mol.) in PhMe (30 ml) at room temperature. The mixture is heated up to 40° C. for 12 h, cooled down to room temperature, washed with NH4Cl (saturated) and the aqueous layer is acidified to pH 3 by addition of HCl (5 N). After 3 extractions with EtOAc, the organic layers are dried over MgSO4, concentrated in vacuo to afford the crude reaction mixture which is purified by chromatography on silicagel (first purification with CH2Cl2/MeOH/NH4OH 98/018/0.02; second purification with EtOAC/iPrOH 95/5; third purification by preparative reverse phase LC/MS) to afford 2-benzyl-4-[(2-oxo-4-propylpyrrolidin-1-yl)methyl]-2,4-dihydro-3H-pyrazol-3-one x281 as a red oil (0.18 g).

Workup

  1. temperaturecooled down to room temperature
  2. washwashed with NH4Cl (saturated)
  3. additionthe aqueous layer is acidified to pH 3 by addition of HCl (5 N)
  4. extractionAfter 3 extractions with EtOAc
  5. dry with materialthe organic layers are dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto afford the crude
  8. customreaction mixture which
  9. customis purified by chromatography on silicagel (first purification with CH2Cl2/MeOH/NH4OH 98/018/0.02; second purification with EtOAC/iPrOH 95/5; third purification by preparative reverse phase LC/MS)

Sources & evidence

ORD record
ord-a837099a222b4ef7ba261765875628d6
Source dataset
uspto-grants-2013_08
Patent number
US08518943B2

Reaction notes

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