HCID 57422445, compound → HCID 57422455, compound

HRID 658702Notes

Reaction equation

HRID 658702 reaction equation
[CH3:1][C:2]1[C:6]([CH2:7][N:8]2[CH:12]=[C:11]([N:13]3[C:17](=[O:18])[CH2:16][N:15]([CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[N+:26]([O-])=O)[C:14]3=[O:29])[CH:10]=[N:9]2)=[C:5]([CH3:30])[O:4][N:3]=1>C(O)C.[Pd]>[NH2:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[CH2:19][N:15]1[CH2:16][C:17](=[O:18])[N:13]([C:11]2[CH:10]=[N:9][N:8]([CH2:7][C:6]3[C:2]([CH3:1])=[N:3][O:4][C:5]=3[CH3:30])[CH:12]=2)[C:14]1=[O:29]

Participants

4

Reactant 1

HCID 57422445HCID 57422445, compound

Product 1

HCID 57422455HCID 57422455, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)-1-(2-nitrobenzyl)imidazolidine-2,4-dione (example 10-23) (126 mg, 0.3 mmol) was dissolved in 2 mL ethanol. The solution was passed through the H-Cube instrument at room temperature using 10% Pd/C catalyst at a flow rate of 1 ml/minute. The collected fraction was concentrated, redissolved in 2 mL ethanol and purified by HPLC (10-95% Acetonitrile/Water, 25 minutes). The purified fractions were combined and concentrated to afford the title compound. Yield 26%. MS M+H calculated 381.1; found 381.1. The title compound was shown to inhibit hT2R08 bitter receptor and had an IC50 of 0.02 uM.

Workup

  1. customwas passed through the H-Cube instrument at room temperature
  2. concentrationThe collected fraction was concentrated
  3. dissolutionredissolved in 2 mL ethanol
  4. custompurified by HPLC (10-95% Acetonitrile/Water, 25 minutes)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0e90ef91ca2844d49245d2d71ad1954f
Source dataset
uspto-grants-2011_12
Patent number
US08076491B2

Reaction notes

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