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Diisopropylethylamine → (R)-2-Oxoimidazolidine-4-carboxylic acid[5-(3-butylphenyl)-1-phenyl-1H-pyrazol-3-yl]amide

HRID 83565
Notes
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Reaction equation

HRID 83565 reaction equation
[CH2:1]([C:5]1[CH:6]=[C:7]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:14]=[C:13]([NH2:22])[CH:12]=2)[CH:8]=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4].[O:23]=[C:24]1[NH:28][C@@H:27]([C:29](O)=[O:30])[CH2:26][NH:25]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C)C=O.O>[CH2:1]([C:5]1[CH:6]=[C:7]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:14]=[C:13]([NH:22][C:29]([C@H:27]3[CH2:26][NH:25][C:24](=[O:23])[NH:28]3)=[O:30])[CH:12]=2)[CH:8]=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 7003745(4R)-2-oxoimidazolidine-4-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 866803825-(3-Butylphenyl)-1-phenyl-1H-pyrazol-3-ylamine

Product 1

HCID 71287781
(R)-2-Oxoimidazolidine-4-carboxylic acid[5-(3-butylphenyl)-1-phenyl-1H-pyrazol-3-yl]amide
Yield 21.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(3-butylphenyl)-1-phenyl-1H-pyrazol-3-ylamine (40 mg) in N,N-dimethylformamide (0.4 ml) were sequentially added (R)-2-oxoimidazolidine-4-carboxylic acid (21 mg) prepared by the same procedures as Preparation 20, HATU (63 mg), diisopropylethylamine (29 μL) at room temperature, and the mixture was stirred for 2 hours. To this reaction mixture was added water, and the mixture was extracted with ethyl acetate. The resulting 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. The resulting residue was purified by silica gel thin-layer chromatography (eluent: n-hexane/acetone=1/5). To the resulting solid was added diisopropyl ether, 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 (12 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe resulting 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: n-hexane/acetone=1/5)
  6. additionTo the resulting solid was added diisopropyl ether
  7. stirringthe mixture was stirred
  8. filtrationA solid was collected from this suspension by filtration
  9. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-c729d6718d8f41089a0dba673ac2657e
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846746B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes