Diisopropylethylamine → HCID 59170086, compound

HRID 1446264Notes

Reaction equation

HRID 1446264 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.[CH2:43]([C:47]1[O:51][N:50]=[CH:49][C:48]=1[C:52](O)=[O:53])[CH2:44][CH2:45][CH3:46]>CN(C=O)C>[CH2:43]([C:47]1[O:51][N:50]=[CH:49][C:48]=1[C:52]([N: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)=[O:53])[CH2:44][CH2:45][CH3:46]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 36136513-(Pyrrolidin-3-yl)pyridineHCID 59170067HCID 59170067, compound

Product 1

HCID 59170086HCID 59170086, compoundYield 26.7%

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-butylisoxazole-4-carboxylic acid (17 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 (8 mg). MS (ESI, pos. ion) m/z calcd for C17H21N3O2: 299.1634, found 299.1635.

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-4b1384ed1f7c40b790e6e447738eeb4f
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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