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Diisopropylethylamine → 2-{4-[(3-Pyridin-3-ylpyrrolidin-1-yl)carbonyl]isoxazol-5-yl}pyridine

HRID 1446265
Notes
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Reaction equation

HRID 1446265 reaction equation
[NH:1]1[CH2:5][CH2:4][CH:3]([C:6]2[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=2)[CH2:2]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)C(C)C)C.[N:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[C:49]1[O:53][N:52]=[CH:51][C:50]=1[C:54](O)=[O:55]>CN(C=O)C>[N:8]1[CH:9]=[CH:10][CH:11]=[C:6]([CH:3]2[CH2:4][CH2:5][N:1]([C:54]([C:50]3[CH:51]=[N:52][O:53][C:49]=3[C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][N:43]=3)=[O:55])[CH2:2]2)[CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 36136513-(Pyrrolidin-3-yl)pyridineHCID 223090705-(Pyridin-2-yl)-1,2-oxazole-4-carboxylic acid

Product 1

HCID 591702042-{4-[(3-Pyridin-3-ylpyrrolidin-1-yl)carbonyl]isoxazol-5-yl}pyridine

Reagents, catalysts & solvents

1
HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-pyrrolidin-3-yl-pyridine (15 mg, 0.1 mmol), TBTU (48 mg, 0.15 mmol, 1.5 equ.) and N-ethyl-N-isopropylpropan-2-amine (17 μL, 0.1 mmol) in DMF (0.6 mL) was added to 5-pyridin-2-ylisoxazole-4-carboxylic acid (19 mg, 0.1 mmol) and the reaction mixture was stirred at rt for 2 h. The solvent was evaporated and the crude product was purified by RP-HPLC. After evaporation of the solvents from the pure fractions, the residue was dissolved in chloroform and washed with diluted NaOH to provide the neutral compound in the organic phase that was dried (Na2SO4) and evaporated and dried in vacuum to yield the title compound as (12 mg). MS (ESI, pos. ion) m/z calcd for C18H16N4O2: 320.1273, found 320.1273.

Workup

  1. customThe solvent was evaporated
  2. customthe crude product was purified by RP-HPLC
  3. customAfter evaporation of the solvents from the pure fractions
  4. dissolutionthe residue was dissolved in chloroform
  5. washwashed with diluted NaOH
  6. customto provide the neutral compound in the organic phase that
  7. dry with materialwas dried (Na2SO4)
  8. customevaporated
  9. customdried in vacuum

Sources & evidence

ORD record
ord-fb35fa38ba3241e198ec71e259b59213
Source dataset
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07666888B2

Reaction notes

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