5-(4-Ethylphenyl)-1-(morpholin-4-ylcarbonyl)-N-(prop-2-yn-1-yl)piperidine-3-carboxamide → [3-(4-Ethylphenyl)-5-(5-methyl-1,3-oxazol-2-yl)piperidin-1-yl](morpholin-4-yl)methanone

HRID 1643114Notes

Reaction equation

[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][N:13]([C:15]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[O:16])[CH2:12][CH:11]([C:23]([NH:25][CH2:26][C:27]#[CH:28])=[O:24])[CH2:10]2)=[CH:5][CH:4]=1)[CH3:2]>C(#N)C.[Au](Cl)(Cl)Cl>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:10][CH:11]([C:23]3[O:24][C:27]([CH3:28])=[CH:26][N:25]=3)[CH2:12][N:13]([C:15]([N:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)=[O:16])[CH2:14]2)=[CH:5][CH:4]=1)[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

50 mg (0.13 mmol) of the compound from Example 199A were initially charged in 0.5 ml of acetonitrile, and 2 mg (0.01 mmol) of gold trichloride were added. The reaction mixture was stirred at 50° C. for 16 h, concentrated and purified by preparative HPLC. Yield: 10 mg (15% of theory).

Workup

concentrationconcentrated
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-b60543e12b3643f38afbed1635a184d9
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119663B2

Reaction notes

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