Pyridine → HCID 24809856, compound

HRID 1446156Notes

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.Cl.Cl.[NH:50]1[CH2:54][CH2:53][CH:52]([C:55]2[CH:60]=[N:59][CH:58]=[CH:57][N:56]=2)[CH2:51]1>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:50]2[CH2:54][CH2:53][CH:52]([C:55]3[CH:60]=[N:59][CH:58]=[CH:57][N:56]=3)[CH2:51]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 2-pyrrolidin-3-yl-pyrazine trihydrochloride (36 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 (26 mg). HRMS (ESI, pos. ion) m/z calcd for C19H15F3N4O2: 388.1147, found 388.1152.

Workup

customThe residue was purified on reversed phase HPLC

Sources & evidence

ORD record: ord-2883d8512b9d4b6d867afa73b881e9cf
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07666888B2

Reaction notes

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