Pyridine → HCID 135451069, compound

HRID 494551Notes

Reaction equation

HRID 494551 reaction equation
Cl.[NH2:2][C:3]1[CH:36]=[CH:35][C:6]2[NH:7][C:8]([C:13]3[C:14](=[O:34])[C:15]([CH2:25][CH2:26][CH2:27][CH:28]4[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]4)([CH3:24])[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:37](Cl)([CH3:40])(=[O:39])=[O:38].N1C=CC=CC=1>CC(C)=O>[CH:28]1([CH2:27][CH2:26][CH2:25][C:15]2([CH3:24])[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:22]([OH:23])=[C:13]([C:8]3[NH:7][C:6]4[CH:35]=[CH:36][C:3]([NH:2][S:37]([CH3:40])(=[O:39])=[O:38])=[CH:4][C:5]=4[S:10](=[O:12])(=[O:11])[N:9]=3)[C:14]2=[O:34])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 136403544HCID 136403544, compound

Product 1

HCID 135451069HCID 135451069, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of Example 38B (0.357 g, 0.674 mmol), mesyl chloride (0.209 mL, 2.69 mmol), and pyridine (0.436 mL, 5.39 mmol) in acetone (15 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 (0.339 g, 88%).

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-5e8141c6461348a7a770c65f72ca8dfd
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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