Dimethylformamide → HCID 66751117, compound

HRID 534887Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2[CH:20]=[N:21][C:22](Cl)=[CH:23][CH:24]=2)=[O:18])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].[C:26]([O:30][CH2:31][CH3:32])(=[O:29])[CH2:27][SH:28].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2[CH:24]=[CH:23][C:22]([S:28][CH2:27][C:26]([O:30][CH2:31][CH3:32])=[O:29])=[N:21][CH:20]=2)=[O:18])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1-(2-tert-butylphenyl)-4-[(6-chloropyridin-3-yl)carbonyl]piperazine obtained in Example 18 (590 mg), ethyl thioglycolate (361 mg), potassium carbonate (691 mg), and N,N-dimethylformamide (10 mL) was stirred at 80° C. for 2 h. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by flash column chromatography (silica gel, 50:50-0:100 hexane/ethyl acetate) to provide the title compound (430 mg, 59%) as a solid.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe ethyl acetate layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by flash column chromatography (silica gel, 50:50-0:100 hexane/ethyl acetate)

Sources & evidence

ORD record: ord-bad798b0f3874110acae820f4f1930b6
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853215B2

Reaction notes

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