1-Hydroxybenzotriazole → 5-Oxotetrahydrofuran-3-carboxylic acid [1-phenyl-5-(3-propylphenyl)-1H-pyrazol-3-yl]amide

HRID 83523Notes

Reaction equation

HRID 83523 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.[O:22]=[C:23]1[O:27][CH2:26][CH:25]([C:28](O)=[O:29])[CH2:24]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.C(=O)([O-])O.[Na+]>CN(C)C=O.O1CCCC1.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]([CH:25]3[CH2:24][C:23](=[O:22])[O:27][CH2:26]3)=[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 110516762-Oxooxolane-4-carboxylic acidHCID 712877391-Phenyl-5-(3-propylphenyl)-1H-pyrazol-3-ylamine

Product 1

HCID 712877685-Oxotetrahydrofuran-3-carboxylic acid [1-phenyl-5-(3-propylphenyl)-1H-pyrazol-3-yl]amideYield 62.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

To a solution of 1-phenyl-5-(3-propylphenyl)-1H-pyrazol-3-ylamine (109 mg) prepared according to the same procedures as Preparation 8 in N,N-dimethylformamide/tetrahydrofuran (1/1, 2 ml) were sequentially added 5-oxotetrahydrofuran-3-carboxylic acid (82 mg) prepared in Preparation 9, HOBt.H2O (96 mg) and WSC.HCl (121 mg), and the mixture was stirred at room temperature overnight. To this reaction solution was added a saturated aqueous solution of sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The separated organic layer was concentrated under reduced pressure, and the resulting residue was purified by silica gel thin-layer chromatography (eluent: chloroform/methanol=10/1) to give the titled compound (96 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. concentrationThe separated organic layer was concentrated under reduced pressure
  3. customthe resulting residue was purified by silica gel thin-layer chromatography (eluent: chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-dbfc8e69898741b3a4ae3b4587b7a509
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Reaction notes

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