Diisopropylethylamine → 3-(1-{[3-(4-Methoxyphenyl)isoxazol-4-yl]carbonyl}pyrrolidin-3-yl)pyridine

HRID 1446346Notes

Reaction equation

HRID 1446346 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.[NH:48]1[CH2:52][CH2:51][CH:50]([C:53]2[CH:54]=[N:55][CH:56]=[CH:57][CH:58]=2)[CH2:49]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:48]3[CH2:52][CH2:51][CH:50]([C:53]4[CH:54]=[N:55][CH:56]=[CH:57][CH:58]=4)[CH2:49]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 36136513-(Pyrrolidin-3-yl)pyridineHCID 591701213-(4-Methoxyphenyl)isoxazole-4-carboxylic acid

Product 1

HCID 591700373-(1-{[3-(4-Methoxyphenyl)isoxazol-4-yl]carbonyl}pyrrolidin-3-yl)pyridineYield 85.9%

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-pyrrolidin-3-ylpyridine (4 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 (9 mg). MS (ESI, pos. ion) m/z: calcd for C20H19N3O3: 349.1426, found 349.1427.

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-9ae7133012e143df8140884af768e37b
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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