Chloride → HCID 22734208, compound

HRID 1057883Notes

Reaction equation

HRID 1057883 reaction equation
O[CH2:2][C:3]1[C:8]2[CH2:9][C:10]([CH3:13])([CH3:12])[O:11][C:7]=2[C:6]([O:14][CH3:15])=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.[Cl-].[SH:26][C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1>C(Cl)Cl.O>[CH3:15][O:14][C:6]1[C:7]2[O:11][C:10]([CH3:13])([CH3:12])[CH2:9][C:8]=2[C:3]([CH2:2][S:26][C:27]2[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=2)=[CH:4][CH:5]=1

Participants

7

Reactant 4

HCID 312ChlorideHCID 81531DiisopropylethylamineHCID 22734077HCID 22734077, compoundHCID 178418431pyridine-4-thiol

Product 1

HCID 22734208HCID 22734208, compoundYield 48.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Compound 48a (2.0 g) obtained in Step A was dissolved in methylene chloride (100 ml), and then diisopropylethylamine (5.0 ml) and methanesulfonyl.chloride (0.8 ml) were added thereto, followed by stirring at room temperature for one hour. At the same temperature, 4-mercaptopyridine (1.4 g) was added to the reaction solution, and the mixture was stirred for 30 minutes. Water was added to the reaction solution and the mixture was extracted with methylene chloride. The organic layer was washed with a saturated saline and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=30/1) to give Compound 48 (1.4 g, 48.3%) as colorless crystals.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. extractionthe mixture was extracted with methylene chloride
  3. washThe organic layer was washed with a saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform/methanol=30/1)

Sources & evidence

ORD record
ord-e1ad4fb4047e499eb65188bf1ccd3e82
Source dataset
uspto-grants-2003_02
Patent number
US06514996B2

Reaction notes

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