Pyridine → HCID 22724359, compound

HRID 2086842Notes

Reaction equation

HRID 2086842 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:8]2[C:13](=[O:14])[C:12]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:11][C:10]3[CH:22]=[CH:23][CH:24]=[N:25][C:9]2=3)[CH:5]=[CH:6][CH:7]=1.[CH2:26]([S:33](Cl)(=[O:35])=[O:34])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.N1C=CC=CC=1.C(OCC)(=O)C>O1CCOCC1.O>[CH2:26]([S:33]([NH:1][C:2]1[CH:3]=[C:4]([N:8]2[C:13](=[O:14])[C:12]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:11][C:10]3[CH:22]=[CH:23][CH:24]=[N:25][C:9]2=3)[CH:5]=[CH:6][CH:7]=1)(=[O:35])=[O:34])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 74740Phenylmethanesulfonyl chlorideHCID 22724309HCID 22724309, compound

Product 1

HCID 22724359HCID 22724359, compoundYield 22.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 4-(3-aminophenyl)-3-oxo-2-benzyl-3,4-dihydropyrido[2,3-b]pyrazine (150 mg), benzylsulfonyl chloride (96 mg) and pyridine (0.04 ml) in 1,4-dioxane (3 ml) was stirred at 80° C. for 2 hours. The mixture was poured into a mixture of ethyl acetate and water. The organic phase was washed with water and brine, dried over magnesium sulfate, concentrated, and subjected to silica gel column chromatography (hexane-ethyl acetate 1:1) to afford 4-(3-benzylsulfonylaminophenyl)-3-oxo-2-benzyl-3,4-dihydropyrido[2,3-b]pyrazine (49 mg) as a solid.

Workup

  1. washThe organic phase was washed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-24d79f62127c4e85a21262446019625a
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

Loading…