Methanesulfonyl chloride → HCID 22388202, compound

HRID 1072906Notes

Reaction equation

HRID 1072906 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:11]3=[N:12][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:15]=[C:10]3[N:9]=[C:8]2[CH3:20])=[C:4]([Cl:23])[CH:3]=1.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>N1C=CC=CC=1>[Cl:23][C:4]1[CH:3]=[C:2]([NH:1][S:25]([CH3:24])(=[O:27])=[O:26])[CH:22]=[CH:21][C:5]=1[CH2:6][N:7]1[C:11]2=[N:12][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:15]=[C:10]2[N:9]=[C:8]1[CH3:20]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chloride2×HCID 22388007HCID 22388007, compound

Product 1

HCID 22388202HCID 22388202, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent3×

Procedure

Methyl 3-(4-amino-2-chlorobenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylate (150 mg) was dissolved in pyridine (1.5 ml), and a solution of methanesulfonyl chloride (114 mg) in pyridine (0.5 ml) was added at room temperature. The mixture was refluxed under heating for 1 hr. Thereto was added a solution of methanesulfonyl chloride (114 mg) in pyridine (0.5 ml) at room temperature, and the mixture was left standing overnight at room temperature. The reaction mixture was concentrated under reduced pressure and ice water was added to the residue. The resulting product was extracted with chloroform. The organic layer was washed successively with a saturated aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and filtrated. The filtrate was concentrated under reduced pressure. Ethanol was added to the residue, and the crystals were washed, filtrated and dried under reduced pressure to give the objective compound (101 mg) as pale-yellow crystals.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for 1 hr
  3. waitthe mixture was left
  4. concentrationThe reaction mixture was concentrated under reduced pressure and ice water
  5. additionwas added to the residue
  6. extractionThe resulting product was extracted with chloroform
  7. washThe organic layer was washed successively with a saturated aqueous sodium hydrogencarbonate solution and saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltrated
  10. concentrationThe filtrate was concentrated under reduced pressure
  11. additionEthanol was added to the residue
  12. washthe crystals were washed
  13. filtrationfiltrated
  14. customdried under reduced pressure

Sources & evidence

ORD record
ord-2a09c7f4158a42d98f0ad04de671c12c
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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