Triethylamine → 4-{[4,5-Bis(3-chlorophenyl)furan-2-yl]carbonyl}piperazin-2-one

HRID 2190145Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([C:20](O)=[O:21])[O:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)[CH:5]=[CH:6][CH:7]=1.S(Cl)(Cl)=O.C(N(CC)CC)C.[NH:34]1[CH2:39][CH2:38][NH:37][CH2:36][C:35]1=[O:40]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([C:20]([N:37]3[CH2:38][CH2:39][NH:34][C:35](=[O:40])[CH2:36]3)=[O:21])[O:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

600 mg (1.07 mmol) of the compound from Example 25A are provided in 14 ml of dry toluene, 0.24 ml (3.22 mmol) of thionyl chloride are added and the mixture is heated under reflux for 2.5 hours. The reaction mixture is concentrated, and the residue is taken up in 10 ml of dichloromethane and cooled to 0° C. 0.24 ml (1.72 mmol) of triethylamine and then 172 mg (1.72 mmol) of piperazin-2-one are then added, and the reaction mixture is stirred at RT overnight. The mixture is subsequently concentrated and the residue is purified by preparative HPLC (RP18 column; eluent: acetonitrile/water gradient). 302 mg (68% of theory) of the title compound are obtained.

Workup

temperaturethe mixture is heated
temperatureunder reflux for 2.5 hours
concentrationThe reaction mixture is concentrated
concentrationThe mixture is subsequently concentrated
customthe residue is purified by preparative HPLC (RP18 column; eluent: acetonitrile/water gradient)

Sources & evidence

ORD record: ord-a7ce85e68c684580bc85b092a83f9487
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324268B2

Reaction notes

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