Methanesulfonyl chloride → HCID 67391150, compound

HRID 910625Notes

Reaction equation

HRID 910625 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:41])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[C:11]=2[NH:17][C:18](=[O:40])[C:19]2[CH:24]=[CH:23][C:22]([C:25]3[C:26](=[O:39])[N:27]([CH2:31][CH2:32][N:33]4[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]4)[CH:28]=[CH:29][CH:30]=3)=[CH:21][CH:20]=2)=[N:6][CH:7]=1.[CH3:42][S:43](Cl)(=[O:45])=[O:44]>N1C=CC=CC=1>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:41])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[C:11]=2[NH:17][C:18](=[O:40])[C:19]2[CH:24]=[CH:23][C:22]([C:25]3[C:26](=[O:39])[N:27]([CH2:31][CH2:32][N:33]4[CH2:34][CH2:35][N:36]([S:43]([CH3:42])(=[O:45])=[O:44])[CH2:37][CH2:38]4)[CH:28]=[CH:29][CH:30]=3)=[CH:21][CH:20]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 57584073HCID 57584073, compound

Product 1

HCID 67391150HCID 67391150, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

N-(5-chloropyridin-2-yl)-3-hydroxy-2-({4-[2-oxo-1-(2-piperazin-1-ylethyl)-1,2-dihydropyridin-3-yl]benzoyl}amino)benzamide (130 mg) was dissolved in pyridine (5 mL), and with cooling with ice, methanesulfonyl chloride (51 μL) was added, followed by stifling at room temperature for 4 hours. The reaction mixture was concentrated under reduced pressure, then azeotroped with toluene. An aqueous saturated sodium hydrogencarbonate solution was added to the residue, followed by extraction with chloroform. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by NH-silica gel column chromatography (methanol/chloroform=0% to 5%), then by silica gel column chromatography (methanol/chloroform=0% to 5%). The resulting compound was dissolved in ethyl acetate, and 4 N hydrochloric acid/ethyl acetate was added, followed by stirring at room temperature for 30 minutes. The precipitate was collected by filtration and dried under reduced pressure to obtain N-(5-chloropyridin-2-yl)-3-hydroxy-2-{[4-(1-{2-[4-(methylsulfonyl)piperazin-1-yl]ethyl}-2-oxo-1,2-dihydropyridin-3-yl)benzoyl]amino}benzamide hydrochloride (47 mg) as a yellow white solid.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customazeotroped with toluene
  4. additionAn aqueous saturated sodium hydrogencarbonate solution was added to the residue
  5. extractionfollowed by extraction with chloroform
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by NH-silica gel column chromatography (methanol/chloroform=0% to 5%)
  9. dissolutionThe resulting compound was dissolved in ethyl acetate
  10. addition4 N hydrochloric acid/ethyl acetate was added
  11. filtrationThe precipitate was collected by filtration
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-427a8717c3854a57b6427e2daebe1049
Source dataset
uspto-grants-2011_09
Patent number
US08022208B2

Reaction notes

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