Hydrochloric Acid → 2-[2-(4-Chloro-phenyl)-5-methyl-thiazol-4-yl]-4-[1-(tetrahydro-pyran-4-yl)-meth-(E)-ylidene]-cyclopentane-1,3-dione

HRID 2170811Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 2-[2-(4-Chloro-phenyl)-5-methyl-thiazol-4-yl]-3-methoxy-5-[1-(tetrahydro-pyran-4-yl)-meth-(E)-ylidene]-cyclopent-2-enone (190 mg, 0.45 mmol) in acetone (2 ml) was added 2N hydrochloric acid (2 ml) and the reaction heated to 120° C. for 30 minutes by microwave irradiation. The crude reaction was diluted with ethyl acetate (25 ml) and washed with saturated aqueous ammonium chloride solution (25 ml), brine (25 ml) and the organic later separated, dried over magnesium sulphate and the solvent removed under reduced pressure to give 2-[2-(4-Chloro-phenyl)-5-methyl-thiazol-4-yl]-4-[1-(tetrahydro-pyran-4-yl)-meth-(E)-ylidene]-cyclopentane-1,3-dione (168 mg).

Workup

customThe crude reaction
washwashed with saturated aqueous ammonium chloride solution (25 ml), brine (25 ml)
dry with materialthe organic later separated, dried over magnesium sulphate
customthe solvent removed under reduced pressure

Sources & evidence

ORD record: ord-8eaccaf4e0634bfb9ce467914baa13e4
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051300B2

Reaction notes

Loading…