Diisopropylethylamine → 1-{[3-(3-Chloro-4-methoxyphenyl)isoxazol-4-yl]carbonyl}-3-(5-methylpyridin-2-yl)pyrrolidin-3-ol

HRID 1446357Notes

Reaction equation

HRID 1446357 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.[CH3:51][C:52]1[CH:53]=[CH:54][C:55]([C:58]2([OH:63])[CH2:62][CH2:61][NH:60][CH2:59]2)=[N:56][CH:57]=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[C:14]([C:15]([N:60]3[CH2:61][CH2:62][C:58]([C:55]4[CH:54]=[CH:53][C:52]([CH3:51])=[CH:57][N:56]=4)([OH:63])[CH2:59]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 686874603-(5-Methylpyridin-2-yl)pyrrolidin-3-ol dihydrochloride

Product 1

HCID 591701761-{[3-(3-Chloro-4-methoxyphenyl)isoxazol-4-yl]carbonyl}-3-(5-methylpyridin-2-yl)pyrrolidin-3-olYield 54.4%

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-(5-methylpyridin-2-yl)pyrrolidin-3-ol dihydrochloride (10 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 (9 mg). MS (ESI, pos. ion) m/z: calcd for C21H20ClN3O4: 413.1142, found 413.1143.

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-57b3343abe564b13941c245181b98d49
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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