Acetonitrile → HCID 86676327, compound

HRID 1023024Notes

Reaction equation

[OH:1][N:2]=[C:3]([C:5]1[N:6]=[C:7]([CH:10]2[CH2:15][CH2:14][N:13]([C:16](=[O:28])[CH2:17][N:18]3[C:22]([CH3:23])=[CH:21][C:20]([C:24]([F:27])([F:26])[F:25])=[N:19]3)[CH2:12][CH2:11]2)[S:8][CH:9]=1)[CH3:4].Br[CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:44](#N)[CH3:45]>ClCCl>[CH3:23][C:22]1[N:18]([CH2:17][C:16]([N:13]2[CH2:14][CH2:15][CH:10]([C:7]3[S:8][CH:9]=[C:5]([C:3](=[N:2][O:1][CH2:44][CH2:45][CH2:30][CH2:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH3:4])[N:6]=3)[CH2:11][CH2:12]2)=[O:28])[N:19]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:21]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 1-[4-[4-[1-(hydroxyimino)ethyl)-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone (0.5 g, 1.2 mmol) (i.e. the product of Example 1, Step E), (2-bromoethyl)benzene (0.277 g, 1.5 mmol), and cesium carbonate (0.487 g, 1.5 mmol) in acetonitrile (6 mL) was heated at 60° C. overnight, diluted with dichloromethane, and filtered through a fritted SPE tube (Varian® bond elute reservoir). The reaction was concentrated under reduced pressure and the resulting residue purified via silica gel chromatography (hexanes: ethyl acetate gradient) to provide 0.17 g of the title compound.

Workup

filtrationfiltered through a fritted SPE tube
wash(Varian® bond elute reservoir)
concentrationThe reaction was concentrated under reduced pressure
customthe resulting residue purified via silica gel chromatography (hexanes: ethyl acetate gradient)

Sources & evidence

ORD record: ord-a5fd347491cf485888633ae24020196c
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722678B2

Reaction notes

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