Pyridine → HCID 59656663, compound

HRID 2054899Notes

Reaction equation

HRID 2054899 reaction equation
[NH2:1][C:2]1[C:3]2[C:13]([O:14][CH2:15][CH3:16])=[CH:12][CH:11]=[C:10]([NH2:17])[C:4]=2[S:5][C:6]=1[C:7]([NH2:9])=[O:8].N1C=CC=CC=1.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>C1COCC1.O>[NH2:1][C:2]1[C:3]2[C:13]([O:14][CH2:15][CH3:16])=[CH:12][CH:11]=[C:10]([NH:17][S:25]([CH3:24])(=[O:27])=[O:26])[C:4]=2[S:5][C:6]=1[C:7]([NH2:9])=[O:8]

Participants

6

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 59656671HCID 59656671, compound

Product 1

HCID 59656663HCID 59656663, compoundYield 7.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of the above amide (0.2 g, 0.8 mmol) and pyridine (2.0 mL) in THF at 0° C. was added methanesulfonyl chloride (0.46 g, 4.0 mmol). The reaction was stirred at room temperature overnight. It was next diluted with water and extracted with dichloromethane (20 mL). The solvent was removed and purified by preparative TLC (5% EtOAc in CH2Cl2) to afford the title compound (20 mg, 7.6%).

Workup

  1. extractionextracted with dichloromethane (20 mL)
  2. customThe solvent was removed
  3. custompurified by preparative TLC (5% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-4a4e5b37f6e94354b7b3a27011aa7df8
Source dataset
uspto-grants-2008_02
Patent number
US07329764B2

Reaction notes

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