Diisopropylethylamine → 1-{[3-(4-Methoxyphenyl)isoxazol-4-yl]carbonyl}-3-(6-methylpyridin-3-yl)pyrrolidin-3-ol

HRID 1446348Notes

Reaction equation

HRID 1446348 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.[CH3:50][C:51]1[N:56]=[CH:55][C:54]([C:57]2([OH:62])[CH2:61][CH2:60][NH:59][CH2:58]2)=[CH:53][CH:52]=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:59]3[CH2:60][CH2:61][C:57]([C:54]4[CH:55]=[N:56][C:51]([CH3:50])=[CH:52][CH:53]=4)([OH:62])[CH2:58]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 686861923-(6-Methylpyridin-3-yl)pyrrolidin-3-ol dihydrochloride

Product 1

HCID 591702641-{[3-(4-Methoxyphenyl)isoxazol-4-yl]carbonyl}-3-(6-methylpyridin-3-yl)pyrrolidin-3-olYield 26.4%

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-(6-methylpyridin-3-yl)pyrrolidin-3-ol dihydrochloride (8 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 (3 mg). MS (ESI, pos. ion) m/z: calcd for C21H21N3O4: 379.1532, found 379.1529.

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-7dc22b1d380246c0b9cfff32949a3788
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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