Thiazolidinedione → HCID 53250037, compound

HRID 1751183Notes

Reaction equation

HRID 1751183 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH:8]=O)[CH:5]=[C:4]([O:10][CH3:11])[N:3]=1.[S:12]1[CH2:16][C:15](=[O:17])[NH:14][C:13]1=[O:18].[C:19]1([CH3:31])[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:21][CH:20]=1>C(O)C>[CH3:11][O:10][C:4]1[N:3]=[C:2]([N:28]2[CH2:29][CH2:30][N:25]([C:22]3[CH:23]=[CH:24][C:19]([CH3:31])=[CH:20][CH:21]=3)[CH2:26][CH2:27]2)[N:7]=[C:6](/[CH:8]=[C:16]2/[C:15](=[O:17])[NH:14][C:13](=[O:18])[S:12]/2)[CH:5]=1

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 831131-(p-Tolyl)piperazineHCID 58312935HCID 58312935, compound

Product 1

HCID 53250037HCID 53250037, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

Crude 2-chloro-6-methoxypyrimidine-4-carbaldehyde (sad105-058, 76 mg) was dissolved in ethanol (2 mL) and was added to a 10 mL vial containing the thiazolidine-dione (42.8 mg, 0.37 mmol., 1 equiv.) and the 1-(p-tolyl)piperazine (70.8 mg, 0.40 mmol, 1.1 equiv.). The mixture was shaken for 45 h at 80° C. and for 15 h at 90° C. producing a precipitate. LC-MS of the solution showed some product at (M+1=412) and some intermediate at (M+1=430). The desired product crashed out of the solution and the LC-MS of the solution does not reflect well the conversion of the reaction. The yellow solid was filtered using a Pasteur pipette through a pad of glass wool and the solid was rinsed with EtOH (4×0.5 mL). The ethanol filtrate contains some desired product. The solid was re-dissolved in CH2Cl2 and the insoluble solid was filtered off. The filtrate was concentrated under reduced pressure to provide 20 mg of the desired product (Z)-5-((6-methoxy-2-(4-(p-tolyl)piperazin-1-yl)pyrimidin-4-yl)methylene)thiazolidine-2,4-dione (97.3% pure). The insoluble solid was partitioned between saturated NaHCO3 (3 mL) and CH2Cl2 (2×5 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure to provide an additional 13.4 mg of the desired product (total 33.4 mg, 150 mg theoretical, 22%). LC-MS m/z: 412 (M+1).

Workup

  1. additionwas added to a 10 mL
  2. customproducing a precipitate

Sources & evidence

ORD record
ord-c3831b3b283942c589adf1b128f617b3
Source dataset
uspto-grants-2015_10
Patent number
US09157077B2

Reaction notes

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