Pyridine → 2-[1-({5-[4-(Trifluoromethyl)phenyl]isoxazol-4-yl}carbonyl)piperidin-3-yl]propan-2-ol

HRID 1446157Notes

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.Cl.[CH3:48][C:49]([CH:52]1[CH2:57][CH2:56][CH2:55][NH:54][CH2:53]1)([OH:51])[CH3:50]>C(#N)C>[F:17][C:2]([F:1])([F:18])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:13][N:12]=[CH:11][C:10]=2[C:14]([N:54]2[CH2:55][CH2:56][CH2:57][CH:52]([C:49]([OH:51])([CH3:50])[CH3:48])[CH2:53]2)=[O:16])=[CH:7][CH:8]=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-(1-methyl-1-hydroxyethyl)piperidine hydrochloride (25 mg, 0.14 mmol), and stirred at 60° C. for 30 min. The residue was purified on reversed phase HPLC to yield the title compound (23 mg). HRMS (ESI, pos. ion) m/z calcd for C19H21F3N2O3: 382.1504, found 382.1502.

Workup

customThe residue was purified on reversed phase HPLC

Sources & evidence

ORD record: ord-e6b0577ca77e4ce58f4da8558fc4bf37
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07666888B2

Reaction notes

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