1-Hydroxybenzotriazole → (R)-5-Oxopyrrolidine-3-carboxylic acid [1-phenyl-5-(3-trifluoromethoxyphenyl)-1H-pyrazol-3-yl]amide

HRID 83506Notes

Reaction equation

HRID 83506 reaction equation
[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:22])([F:21])[F:20])[CH:13]=3)=[CH:10][C:9]([NH2:23])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:24]=[C:25]1[NH:29][CH2:28][C@H:27]([C:30](O)=[O:31])[CH2:26]1.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]([O:18][C:19]([F:22])([F:20])[F:21])[CH:13]=3)=[CH:10][C:9]([NH:23][C:30]([C@@H:27]3[CH2:26][C:25](=[O:24])[NH:29][CH2:28]3)=[O:31])=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 28063204(3R)-5-oxopyrrolidine-3-carboxylic acidHCID 712877301-Phenyl-5-(3-(trifluoromethoxy)phenyl)-1H-pyrazol-3-ylamine

Product 1

HCID 89465736(R)-5-Oxopyrrolidine-3-carboxylic acid [1-phenyl-5-(3-trifluoromethoxyphenyl)-1H-pyrazol-3-yl]amideYield 83.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-phenyl-5-(3-(trifluoromethoxy)phenyl)-1H-pyrazol-3-ylamine (40 mg) prepared according to the same procedures as Preparation 2 in N,N-dimethylformamide (0.3 ml) were sequentially added (R)-5-oxopyrrolidine-3-carboxylic acid (24 mg) prepared in Preparation 5, HOBt.H2O (29 mg) and WSC.HCl (36 mg), and the mixture was stirred at room temperature overnight. To this reaction solution were added a saturated aqueous solution of sodium hydrogen carbonate and water, and the mixture was stirred. The insoluble substance was collected by filtration, washed with water, and dried under reduced pressure to give the titled compound (45 mg).

Workup

  1. filtrationThe insoluble substance was collected by filtration
  2. washwashed with water
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-f66e1398412346f0853f70e6f1cedcf1
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Reaction notes

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