Pyridine → HCID 71667941, compound

HRID 1507437Notes

Reaction equation

HRID 1507437 reaction equation
[OH:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([C:6](=[O:20])[C:7]([CH3:19])=[C:8]([CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[O:9]2)=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:27](Cl)(=[O:31])[O:28][CH2:29][CH3:30]>CN(C)C=O>[OH:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([C:6](=[O:20])[C:7]([CH3:19])=[C:8]([CH:13]3[CH2:18][CH2:17][N:16]([C:27]([O:28][CH2:29][CH3:30])=[O:31])[CH2:15][CH2:14]3)[O:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 117701633HCID 117701633, compound

Product 1

HCID 71667941HCID 71667941, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-hydroxy-3,8-dimethyl-2-(piperidin-4-yl)-4H-chromen-4-one (68 mg, 0.25 mmol) obtained in Example 7-2 and pyridine (22 μL, 0.28 mmol) in dimethylformamide (2 mL), ethyl chlorocarbonate (24 μL, 0.25 mmol) was added dropwise under cooling with ice, and then the mixture was brought back to room temperature and stirred for 2 days. The reaction solution was concentrated, and the obtained residue was purified by reverse-phase HPLC to obtain 60 mg of the title compound (yield: 69%).

Workup

  1. temperatureunder cooling with ice
  2. customwas brought back to room temperature
  3. concentrationThe reaction solution was concentrated
  4. customthe obtained residue was purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-60db4d790ff24a569c4f3d2030eec427
Source dataset
uspto-grants-2015_12
Patent number
US09221811B2

Reaction notes

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