Diisopropylethylamine → 3-(2,4-Dimethoxybenzyl)-4-oxo-3-azabicyclo[3.1.0]hexane-1-carboxylic acid [1-phenyl-5-(3-propylphenyl)-1H-pyrazol-3-yl]amide

HRID 83579

Reaction equation

HRID 83579 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][O:23][C:24]1[CH:40]=[C:39]([O:41][CH3:42])[CH:38]=[CH:37][C:25]=1[CH2:26][N:27]1[C:32](=[O:33])[CH:31]2[C:29]([C:34](O)=[O:35])([CH2:30]2)[CH2:28]1.CCN=C=NCCCN(C)C.Cl.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>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:34]([C:29]34[CH2:30][CH:31]3[C:32](=[O:33])[N:27]([CH2:26][C:25]3[CH:37]=[CH:38][C:39]([O:41][CH3:42])=[CH:40][C:24]=3[O:23][CH3:22])[CH2:28]4)=[O:35])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 712877391-Phenyl-5-(3-propylphenyl)-1H-pyrazol-3-ylamineHCID 866803903-(2,4-Dimethoxybenzyl)-4-oxo-3-azabicyclo[3.1.0]hexane-1-carboxylic Acid

Product 1

HCID 894658043-(2,4-Dimethoxybenzyl)-4-oxo-3-azabicyclo[3.1.0]hexane-1-carboxylic acid [1-phenyl-5-(3-propylphenyl)-1H-pyrazol-3-yl]amideYield 90.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-phenyl-5-(3-propylphenyl)-1H-pyrazol-3-ylamine (3.5 mg) prepared according to the same procedures as Preparation 2-2 in N,N-dimethylformamide (0.5 ml) were sequentially added 3-(2,4-dimethoxybenzyl)-4-oxo-3-azabicyclo[3.1.0]hexane-1-carboxylic acid (3.7 mg) and WSC.HCl (3.6 mg) at room temperature, and the mixture was stirred for 14 hours. To this reaction mixture were added diisopropylethylamine (3.3 μl) and HATU (7.3 mg), and the mixture was stirred at room temperature for additional 72 hours. To this reaction mixture was added water, and the mixture was extracted with ethyl acetate. This organic layer was washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to give the titled compound (6.3 mg).

Workup

  1. customat room temperature
  2. stirringthe mixture was stirred at room temperature for additional 72 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThis organic layer was washed with water
  5. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fde5c8cad4dc4fafaf89f6e45aa25fc3
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Linked notes

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