Pyridine → HCID 59170199, compound

HRID 1446335Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[CH:10][C:9]=2[C:13](Cl)=[O:14])=[CH:4][CH:3]=1.[B-](F)(F)(F)F.CN(C(ON1N=NC2C1=CC=CC=2)=[N+](C)C)C.N1C=CC=CC=1.Cl.[C:45]1([CH:51]([C@H:53]2[CH2:57][CH2:56][CH2:55][NH:54]2)[OH:52])[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>C(#N)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[CH:10][C:9]=2[C:13]([N:54]2[CH2:55][CH2:56][CH2:57][C@@H:53]2[CH:51]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[OH:52])=[O:14])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 5-(4-methylphenyl)isoxazole-4-carbonyl chloride (22 mg, 0.11 mmol) in acetonitrile (5 mL) was added o-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU) (45 mg, 0.14 mmol, 1.3 eq.), pyridine (34 μL, 0.42 mmol, 4 eq.), and phenyl[(2R)-pyrrolidin-2-yl]methanol hydrochloride (25 mg, 0.12 mmol, 1.1 eq.). The reaction mixture was stirred at ambient temperature for 20 h and at 40° C. for an additional 2 h. The solvent was removed, and the residue was purified by preparative reverse-phase HPLC to yield the product as a white solid. HRMS (ESI, pos. ion) m/z calcd for C22H22N2O3: 362.1630, found 362.1625.

Workup

customThe solvent was removed
customthe residue was purified by preparative reverse-phase HPLC

Sources & evidence

ORD record: ord-5fa566a39d484be6b3ce3e274eeab48f
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07666888B2

Reaction notes

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