Diisopropylethylamine → 1-{[3-(4-Methoxyphenyl)isoxazol-4-yl]carbonyl}-3-pyridin-3-ylpyrrolidin-3-ol

HRID 1446347Notes

Reaction equation

HRID 1446347 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]([C:14]([OH:16])=O)=[CH:12][O:11][N:10]=2)=[CH:5][CH:4]=1.C(N(C(C)C)C(C)C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.Cl.Cl.[N:50]1[CH:55]=[CH:54][CH:53]=[C:52]([C:56]2([OH:61])[CH2:60][CH2:59][NH:58][CH2:57]2)[CH:51]=1>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:13]([C:14]([N:58]3[CH2:59][CH2:60][C:56]([C:52]4[CH:51]=[N:50][CH:55]=[CH:54][CH:53]=4)([OH:61])[CH2:57]3)=[O:16])=[CH:12][O:11][N:10]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 591701213-(4-Methoxyphenyl)isoxazole-4-carboxylic acidHCID 686862673-(Pyridin-3-yl)pyrrolidin-3-ol dihydrochloride

Product 1

HCID 591702291-{[3-(4-Methoxyphenyl)isoxazol-4-yl]carbonyl}-3-pyridin-3-ylpyrrolidin-3-olYield 54.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(4-methoxyphenyl)isoxazole-4-carboxylic acid (7 mg, 0.03 mmol), N-ethyl-N-isopropylpropan-2-amine (16 μL, 0.09 mmol, 3 equ.) and TBTU (12 mg, 0.036 mmol, 1.2 equ.) in DMF (0.3 mL) was added to 3-pyridin-3-ylpyrrolidin-3-ol dihydrochloride (7 mg, 0.03 mmol). After 1 h at rt the crude product was purified by RP-HPLC. The pure fractions were basified (NaHCO3) and extracted with ethyl acetate, dried (Na2SO4), evaporated and dried in vacuum to yield the title compound (6 mg). MS (ESI, pos. ion) m/z: calcd for C20H19N3O4: 365.1376, found 365.1375.

Workup

  1. customAfter 1 h at rt the crude product was purified by RP-HPLC
  2. extractionextracted with ethyl acetate
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customdried in vacuum

Sources & evidence

ORD record
ord-d0bed5ea94f84b6d80de60c35ed59ef4
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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