1-Hydroxybenzotriazole → (R)-3-methyl-2-oxoimidazolidine-4-carboxylic acid[1-phenyl-5-(3-propylphenyl)-1H-pyrazol-3-yl]amide

HRID 83520Notes

Reaction equation

HRID 83520 reaction equation
[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][CH2:19][CH3:20])[CH:13]=3)=[CH:10][C:9]([NH2:21])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:22][N:23]1[C@@H:27]([C:28](O)=[O:29])[CH2:26][NH:25][C:24]1=[O:31].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.C(=O)([O-])O.[Na+]>CN(C)C=O.O>[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][CH2:19][CH3:20])[CH:13]=3)=[CH:10][C:9]([NH:21][C:28]([C@H:27]3[CH2:26][NH:25][C:24](=[O:31])[N:23]3[CH3:22])=[O:29])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 712877391-Phenyl-5-(3-propylphenyl)-1H-pyrazol-3-ylamineHCID 86680360HCID 86680360, compound

Product 1

HCID 89465846(R)-3-methyl-2-oxoimidazolidine-4-carboxylic acid[1-phenyl-5-(3-propylphenyl)-1H-pyrazol-3-yl]amideYield 49.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-phenyl-5-(3-propylphenyl)-1H-pyrazol-3-ylamine (56 mg) prepared according to the same procedures as Preparation 8 in N,N-dimethylformamide (0.6 ml) were sequentially added (R)-3-methyl-2-oxoimidazolidine-4-carboxylic acid (38 mg) prepared in Preparation 9, HOBt.H2O (46 mg) and WSC.HCl (58 mg), and the mixture was stirred at room temperature for 2 hours. To this reaction solution were added a saturated aqueous solution of sodium hydrogen carbonate and water, and the mixture was extracted with ethyl acetate. The separated organic layer was washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel thin-layer chromatography (eluent: chloroform/methanol=10/1) to give the titled compound (40 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe separated organic layer was washed with water
  3. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel thin-layer chromatography (eluent: chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-44c1071b94dc44dcbee7f8412b2b78be
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Reaction notes

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