Pyridine → 4-{[3-(2-Chlorophenyl)pyrrolidin-1-yl]carbonyl}-5-[4-(trifluoromethyl)phenyl] isoxazole

HRID 1446159Notes

Reaction equation

[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][N:12]=[CH:11][C:10]=2[C:14]([OH:16])=O)=[CH:5][CH:4]=1.[B-](F)(F)(F)F.CN(C(ON1N=NC2C1=CC=CC=2)=[N+](C)C)C.N1C=CC=CC=1.C(O)(=O)C(O)=O.[Cl:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][C:55]=1[CH:60]1[CH2:64][CH2:63][NH:62][CH2:61]1>C(#N)C>[Cl:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][C:55]=1[CH:60]1[CH2:64][CH2:63][N:62]([C:14]([C:10]2[CH:11]=[N:12][O:13][C:9]=2[C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:18])[F:17])=[CH:8][CH:7]=2)=[O:16])[CH2:61]1

Participants

Conditions

Temperature: 60 °C

Procedure

5-[4-(Trifluoromethyl)phenyl]isoxazole-4-carboxylic acid (30 mg, 0.12 mmol) was dissolved in acetonitrile (1.5 mL) followed by the addition of o-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU) (52 mg, 0.16 mmol), pyridine (60 μL, 0.72 mmol) and 3-(2-chlorophenyl)pyrrolidine oxalate (38 mg, 0.14 mmol), and stirred at 60° C. for 2 h. The residue was purified on reversed phase HPLC to yield the title compound (9 mg). HRMS (ESI, pos. ion) m/z calcd for C21H16ClF3N2O2: 420.0852, found 420.0854.

Workup

customThe residue was purified on reversed phase HPLC

Sources & evidence

ORD record: ord-2fca7695d89d41c7bccb73c4bc3913ee
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07666888B2

Reaction notes

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