Water → HCID 71510401, compound

HRID 83566Notes

Reaction equation

HRID 83566 reaction equation
[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][O:19][CH:20]([C:25]([F:28])([F:27])[F:26])[C:21]([F:24])([F:23])[F:22])[CH:13]=3)=[CH:10][C:9]([NH2:29])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:30]=[C:31]1[NH:35][CH2:34][C@@H:33]([C:36](O)=[O:37])[CH2:32]1.CCN=C=NCCCN(C)C.Cl.O>CN(C)C(=O)C>[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][O:19][CH:20]([C:21]([F:22])([F:23])[F:24])[C:25]([F:28])([F:26])[F:27])[CH:13]=3)=[CH:10][C:9]([NH:29][C:36]([C@H:33]3[CH2:32][C:31](=[O:30])[NH:35][CH2:34]3)=[O:37])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 25100087(S)-5-oxopyrrolidine-3-carboxylic acidHCID 86680383HCID 86680383, compound

Product 1

HCID 71510401HCID 71510401, compoundYield 54.6%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 1-phenyl-5-[3-(2,2,2-trifluoro-1-trifluoromethyl-ethoxymethyl)phenyl]-1H-pyrazol-3-ylamine (78 mg) in N,N-dimethylacetamide (1.0 ml) were sequentially added (S)-5-oxopyrrolidine-3-carboxylic acid (29 mg) prepared according to the same procedures as Preparation 5 and WSC.HCl (44 mg) at room temperature, and the mixture was stirred overnight. To this reaction mixture was added water, and then the precipitated solid was collected by filtration. The resulting solid was purified by silica gel thin-layer chromatography (eluent: chloroform/methanol=9/1). To the resulting solid were added water and a small amount of methanol, and the mixture was stirred. A solid was collected from this suspension by filtration, and was dried under reduced pressure to give the titled compound (54 mg).

Workup

  1. customprepared
  2. filtrationthe precipitated solid was collected by filtration
  3. customThe resulting solid was purified by silica gel thin-layer chromatography (eluent: chloroform/methanol=9/1)
  4. additionTo the resulting solid were added water
  5. stirringa small amount of methanol, and the mixture was stirred
  6. filtrationA solid was collected from this suspension by filtration
  7. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-f460e8149e2749ff967d365424b80201
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Reaction notes

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