Pyridine → HCID 135509839, compound

HRID 494525Notes

Reaction equation

HRID 494525 reaction equation
Cl.[NH2:2][C:3]1[CH:30]=[CH:29][C:6]2[NH:7][C:8]([C:13]3[C:14](=[O:28])[C:15]([CH3:27])([CH2:24][CH2:25][CH3:26])[C:16]4[C:21]([C:22]=3[OH:23])=[CH:20][CH:19]=[CH:18][CH:17]=4)=[N:9][S:10](=[O:12])(=[O:11])[C:5]=2[CH:4]=1.[S:31](Cl)([CH3:34])(=[O:33])=[O:32].N1C=CC=CC=1>CC(C)=O>[OH:23][C:22]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH3:27])([CH2:24][CH2:25][CH3:26])[C:14](=[O:28])[C:13]=1[C:8]1[NH:7][C:6]2[CH:29]=[CH:30][C:3]([NH:2][S:31]([CH3:34])(=[O:33])=[O:32])=[CH:4][C:5]=2[S:10](=[O:12])(=[O:11])[N:9]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 136403579HCID 136403579, compound

Product 1

HCID 135509839HCID 135509839, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of Example 32B (0.050 g, 0.112 mmol), mesyl chloride (0.035 mL, 0.447 mmol), and pyridine (0.073 mL, 0.893 mmol) in acetone (1.5 mL) was stirred at 25° C. for 18 hours. The solution was partitioned between ethyl acetate and dilute citric acid and the layers were separated. The ethyl acetate layer was dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with methylene chloride and 2.5% methanol in methylene chloride to give the desired product (0.049 g, 89%).

Workup

  1. customThe solution was partitioned between ethyl acetate and dilute citric acid
  2. customthe layers were separated
  3. dry with materialThe ethyl acetate layer was dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel eluting with methylene chloride and 2.5% methanol in methylene chloride

Sources & evidence

ORD record
ord-0aa489169d704fd99da445cd1dc72b43
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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