Water → HCID 22388325, compound

HRID 1072924Notes

Reaction equation

HRID 1072924 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.N1C=CC=CC=1.[C:30]1([S:36](Cl)(=[O:38])=[O:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.O>ClCCl>[C:30]1([S:36]([NH:1][C:2]2[CH:22]=[CH:21][C:5]([CH2:6][N:7]3[C:11]4=[N:12][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:15]=[C:10]4[N:9]=[C:8]3[CH3:20])=[C:4]([Cl:23])[CH:3]=2)(=[O:38])=[O:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 22388007HCID 22388007, compound

Product 1

HCID 22388325HCID 22388325, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 3-(4-amino-2-chlorobenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylate (200 mg) in dichloromethane (2 ml) was added pyridine (95.7 mg). Benzenesulfonyl chloride (117 mg) was added under ice-cooling and the mixture was stirred at room temperature for 12 hr. Water was added to the reaction mixture and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Methanol was added to the residue for crystallization, and the crystals were collected by filtration, dried under reduced pressure to give the objective compound (213 mg) as colorless crystals.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with chloroform
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionMethanol was added to the residue for crystallization
  7. filtrationthe crystals were collected by filtration
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-82c7361a4d284e3fb49e55d62147b30d
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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