Triphenylphosphine → Tert-butyl 4-(6-(1-(4-(trifluoromethyl)phenyl)piperidin-4-yloxy)quinoline-3-carboxamido)piperidine-1-carboxylate

HRID 340416Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([NH:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1)=[O:13])=[CH:5]2.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[F:42][C:43]([F:58])([F:57])[C:44]1[CH:49]=[CH:48][C:47]([N:50]2[CH2:55][CH2:54][CH:53](O)[CH2:52][CH2:51]2)=[CH:46][CH:45]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[F:58][C:43]([F:42])([F:57])[C:44]1[CH:45]=[CH:46][C:47]([N:50]2[CH2:55][CH2:54][CH:53]([O:1][C:2]3[CH:3]=[C:4]4[C:9](=[CH:10][CH:11]=3)[N:8]=[CH:7][C:6]([C:12]([NH:14][CH:15]3[CH2:16][CH2:17][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:19][CH2:20]3)=[O:13])=[CH:5]4)[CH2:52][CH2:51]2)=[CH:48][CH:49]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred suspension of the product of step 2 above (0.7 g, 1.88 mmol) in toluene (15 mL) at room temperature was added diisopropyl azodicarboxylate (557 μl, 2.83 mmol), 1-(4-(trifluoromethyl)phenyl)piperidin-4-ol (0.693 g, 2.83 mmol), and triphenyl phosphine (0.742 g, 2.83 mmol). The mixture was stirred at 50° C. overnight and then concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, 3% methanol in methylene chloride) to afford tert-butyl 4-(6-(1-(4-(trifluoromethyl)phenyl)piperidin-4-yloxy)quinoline-3-carboxamido)piperidine-1-carboxylate as a white solid (0.306 g, 27%). LCMS (m/z): 599 (MH+)

Workup

concentrationconcentrated under reduced pressure
customThe residue was purified by flash chromatography (silica gel, 3% methanol in methylene chloride)

Sources & evidence

ORD record: ord-72f51beebea44866883dcbe731a02df0
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895578B2

Reaction notes

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