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

HRID 1446356Notes

Reaction equation

HRID 1446356 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[C:14]([C:15]([OH:17])=O)=[CH:13][O:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].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:51]1[CH:56]=[CH:55][CH:54]=[C:53]([C:57]2([OH:62])[CH2:61][CH2:60][NH:59][CH2:58]2)[CH:52]=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[C:14]([C:15]([N:59]3[CH2:60][CH2:61][C:57]([C:53]4[CH:52]=[N:51][CH:56]=[CH:55][CH:54]=4)([OH:62])[CH2:58]3)=[O:17])=[CH:13][O:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 591701453-(3-Chloro-4-methoxyphenyl)-isoxazole-4-carboxylic acidHCID 686862673-(Pyridin-3-yl)pyrrolidin-3-ol dihydrochloride

Product 1

HCID 591700281-{[3-(3-Chloro-4-methoxyphenyl)isoxazol-4-yl]carbonyl}-3-pyridin-3-ylpyrrolidin-3-olYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(3-chloro-4-methoxyphenyl)-isoxazole-4-carboxylic acid (10 mg, 0.04 mmol), N-ethyl-N-isopropylpropan-2-amine (14 μL, 0.08 mmol, 2 equ.) and TBTU (15 mg, 0.046 mmol, 1.2 equ.) in DMF (0.3 mL) was added to 3-pyridin-3-ylpyrrolidin-3-ol dihydrochloride (9 mg, 0.04 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 (8 mg). MS (ESI, pos. ion) m/z: calcd for C20H18ClN3O4: 399.0986, found 399.0986.

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-43fc551d842042819d2fad8cdf08a228
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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